Compositions and methods for reducing herbicidal injury

ABSTRACT

A method and compositions for reducing injury to crops, especially wheat and sorghum, by acetanilide selective herbicides employing compounds having in common the base structure ##STR1## wherein Y and Y&#39; are oxygen or sulfur.

This invention relates to novel compositions and methods for reducing or nullifying injury to young crop plants by selective herbicides. More specifically, this invention relates to novel compositions and methods for reducing injury to young crop plants by selective herbicides, such as acetanilide herbicides, which comprises treating the habitat of the crop plant or the seed of the crop plant prior to planting, with an antagonistic agent for the selective herbicide.

The acetanilide herbicides such as alachlor, propachlor, butachlor and the like are very useful for controlling certain weeds in the presence of other growing plants. However, many of these herbicides injure certain crop plants, slowing growth and development at application rates necessary to stunt or kill the weeds. As a consequence, certain of these herbicides can not be employed for controlling weeds in the presence of certain crops, some of which crops are important commodities in the world food supply. Obviously, there is a need for a method of reducing or nullifying the injury of the crop plant by the selective acetanilide herbicide while not affecting the herbicidal action on the weed to be controlled.

There is provided by this invention a novel method of reducing or nullifying injury to the desired crop plant by selective acetanilide herbicides which does not interfere with the herbicidal action on the weed to be controlled. There are also provided novel compositions for treating the soil or the crop seed to reduce or nullify injury to the crop by selective acetanilide herbicides.

The compounds which are useful in reducing or eliminating crop injury are sometimes referred to as antagonistic agents, antidote compounds, or safening agents. Antagonistic agents for the purpose of this invention are defined as compounds which counteract the herbicidal action of selective acetanilide herbicides, thereby reducing or nullifying injury to the plant, yet, which exhibit little or no toxicity to the crop or crop seed at effective rates of application. Although the mechanism by which these compounds reduce the herbicidal activity of the acetanilide herbicide on crop plants without reducing the effective control of undesired plants or weeds, is not fully understood, the herbicide test program has confirmed the phenomenon for a wide variety of compounds having in common the base structure ##STR2## wherein Y and Y' are oxygen or sulfur. These compounds when employed with an acetanilide herbicide reduced the injury to crop plants by the acetanilide herbicide, particularly the injury to wheat and sorghum. The compounds which are preferred antagonistic agents with acetanilide hericides for the selective control of undesired plants in the presence of wheat and sorghum are described by the formula ##STR3## wherein Y and Y' are each independently oxygen or sulfur and, when Y and Y' are both oxygen, R is alkyl, alkenyl, haloalkenyl or haloalkynyl. R¹ is hydrogen, alkyl or alkenyl and R² is alkyl, phenyl or substituted phenyl, or R¹ and R² when taken together are alkylene of the emperical formula --C_(n) H_(2n) -- wherein n is an integer of from 4 through 8, inclusive, having from 4 through 8 carbons in a continuous chain between the nitrogen terminal bonds or a group of the formula --C₂ H₄ OC₂ H₄ --; when one of Y and Y' is oxygen, R is alkyl, alkenyl or haloalkenyl, R¹ is hydrogen, alkyl or ##STR4## wherein m is an integer of from 1 to 4 and R² is hydrogen, alkyl, phenyl or substituted phenyl or R¹ and R² when taken together are a group of the formula --C₂ H₄ OC₂ H₄ --or R¹ and R² when taken together, provided that Y is oxygen, are alkylene of the empirical formula --C_(n) H_(2n) -- wherein n is an integer of from 4 through 8, inclusive, having from 4 through 8 carbons in a continuous chain between the nitrogen terminal bonds, or R¹ and R² when taken together, provided that Y' is oxygen, are an unsaturated hydrocarbon of the empirical formula --C_(n) H_(2n-2) wherein n is an integer of from 4 through 8, inclusive, having from 4 through 8 carbons in a continuous chain between the nitrogen terminal bonds; and when both Y an Y' are sulfur, R is alkyl, substituted alkyl, alkenyl, haloalkenyl, phenyl or substituted phenyl, R¹ is alkyl, phenyl or substituted phenyl and R² is hydrogen, alkyl, alkenyl or haloalkenyl or R and R¹ when taken together are alkylene of the empirical formula --C_(n) H_(2n) -- wherein n is an integer of from 4 through 8, inclusive, having from 4 through 8 carbons in a continuous chain between the nitrogen terminal bonds, an unsaturated hydrocarbon of the empirical formula --C_(n) H_(2n-2) wherein n is an integer of from 4 through 8, inclusive, having from 4 through 8 carbons in a continuous chain between the nitrogen terminal bonds or a group of the formula ##STR5## wherein each R³ is independently hydrogen, halo or lower alkyl.

The amount of such antagonistic agents employed in methods and compositions of this invention will vary according to the particular acetanilide herbicide with which the agent is employed and the rate of application of the herbicide. In each instance the amount of antagonistic agent employed is a safening effective amount. By a safening effective amount is meant an amount which reduces crop injury by the acetanilide herbicide. In the tests employed in illustrating this invention, the amount of crop injury was reduced by at least 15 percent. In certain instances, a significant level of reduction of crop injury may be as low as about 10 percent and in other instances no lower than 20 percent. The reduction in level of crop injury is defined as the difference between the observed percentage of crop injury by the acetanilide herbicide without the safening agent and the observed percentage of crop injury by the acetanilide herbicide employed in conjunction with a safening effective amount of an antagonistic agent as defined herein.

Preferred alkyl are aliphatic hydrocarbons having from 1 through 18, inclusive, carbons. The configuration of the structure can be straight-chain, branched-chain, cyclic or a mixed configuration having both branched and cyclic moieties. More preferred alkyl have from 1 through 6, inclusive, carbons.

As employed herein, the terms "lower alkyl" and "lower alkoxy" designate those groups wherein the aliphatic chain is straight or branched and has from 1 through 4 carbons, inclusive.

As employed herein, the term "substituted phenyl" designates phenyl groups of the formula ##STR6## wherein each Z is independently halo, trihalomethyl, hydroxyl, nitro, lower alkyl or lower alkoxy, and x is an integer from 1 through 3, inclusive, provided that no more than two Z's are nitro and that no more than one Z is hydroxyl. The term "halo" designates a halogen atom selected from fluorine, chlorine, bromine and iodine. Preferred halo are chloro and bromo. Preferred trihalomethyl is trifluoromethyl.

Preferred alkenyl have from 2 through 8, inclusive, carbons. More preferred alkenyl have from 3 through 6, inclusive, carbons. Still more preferred alkenyl have 3 carbons and have the unsaturated bond in the 2-position.

Preferred haloalkenyl have from 2 through 8, inclusive, carbons and 1 through 3, inclusive, halogens. More preferred haloalkenyl have from 3 through 6, inclusive, carbons and 1 through 3, inclusive, halogens. Still more preferred haloalkenyl have from 3 through 6, inclusive, carbons and 1 through 3, inclusive, chlorines.

Preferred haloalkynyl have from 2 through 8, inclusive, carbons and 1 through 3, inclusive, halogens. More preferred haloalkynyl have from 3 through 6, inclusive, carbons and 1 through 3, inclusive, halogens. Still more preferred haloalkynyl have from 3 through 6, inclusive, carbons and 1 through 3, inclusive, chlorines.

Preferred substituted alkyl have from 1 through 3, inclusive, substituents selected from the group consisting of cyano, hydroxyl, phenyl, substituted phenyl, phenoxyl and substituted phenoxyl. More preferred substituted alkyl have, in the aliphatic portion of the group, from 1 through 6, inclusive, carbons. Still more preferred substituted alkyl have one substituent selected from the aforementioned group.

The compounds employed herein as antagonistic agents are either known compounds or are readily prepared from known compounds by old methods known to the skilled chemist.

Acetanilide herbicides are widely known in the art. U.S. Pat. No. 2,863,752, 3,442,945, 3,547,620, 3,630,716, and 3,637,847 are but a few of the many patents disclosing acetanilide herbicides which have published in the United States and other countries. Although it has been taught that a wide variety of acetanilides are useful as selective herbicides, it is evident from the prior art that alpha-haloacetanilides are most commercially significant herbicidal acetanilides. Because of the wide usage of alpha-haloacetanilides, these herbicides are the preferred herbicides for safening by the methods and compositions of the present invention. Nevertheless, the present safening methods and compositions are useful for safening the herbicidal acetanilide family of compounds and the instant invention is not limited to only alpha-haloacetanilide herbicides.

Particularly effective safening properties are obtained with selective alpha-haloacetanilides of the formula ##STR7## wherein X is halo, Q is alkylene of the empirical formula --C_(y) H_(2y) wherein y is an integer of from 1 through 8, inclusive, A is oxygen or sulfur, each Z³ independently is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, polyalkoxy, alkoxyalkyl, polyalkoxyalkyl, haloalkyl, hydroxyalkyl, haloalkenyl, oxoalkyl, alkenyloxy and alkyl each of a maximum of 18 carbon atoms; aryl, aryloxyalkyl, haloaryl, haloaryloxyalkyl and arylalkyl of from 6 to 24 carbon atoms; furfuryl; and tetrahydrofurfuryl; or two groups are combined to form a cyclic group of from 2 to 6 carbon atoms selected from the group consisting of ##STR8## wherein T is chlorine, bromine or fluorine, T' is alkyl of a maximum of 6 carbon atoms or acyl of a maximum of 4 carbon atoms, m is an integer of from 0 to 3, inclusive, n is an integer of from 0 to 5, inclusive, and p is an integer of 0 or 1 and each Z¹ independently is hydrogen, halogen, or alkyl each of a maximum of 10 carbon atoms, and each Z² independently is hydrogen, alkyl or alkoxy each of a maximum of 10 carbon atoms.

Particularly good safening of alachlor, propachlor and butachlor herbicides with regard to wheat and sorghum has been found employing the safening methods and compositions of the present invention. These particularly good results with regard to wheat and sorghum are likewise obtained with herbicides of the formula ##STR9## wherein each Z⁵ is independently lower alkyl or hydrogen, Z⁴ is lower alkyl and Q² is alkylene of the empirical formula --C_(z) H_(2z) -- wherein z is an integer of from 1 through 4, inclusive, preferably from 1 through 4, inclusive.

The method and compositions of this invention are illustrated by the following examples.

EXAMPLES 1 THROUGH 180

The safening effectiveness of representative antagonistic agents on representative acetanilide herbicides with respect to wheat and sorghum is shown by the test results presented in Table I. For each antagonistic agent, there is shown the percent inhibition of the plants by the acetanilide herbicide and the antagonistic agent and the safening effect of the antagonistic agent in terms of reduction in percent control which is determined by subtracting the percent control of the acetanilide herbicide in a specified amount and the antagonistic agent in a specified amount from the percent control of the acetanilide herbicide in the same specified amount but with no antagonistic agent. These results are obtained by the following procedure:

A good grade of top soil is placed in an aluminum pan and compacted to a depth of 3/8 to 1/2 inch from the top of the pan. A predetermined number of seeds of each of the plant species to be tested are placed on top of the soil in the pans. A quantity of soil sufficient to substantially fill the pan is measured and placed in suitable container. A measured quantity of the antagonistic agent dispersed or dissolved in a suitable carrier is sprayed on the soil in the container. A measured quantity of the acetanilide herbicide dispersed or dissolved in a suitable carrier is then sprayed on the soil in the container already treated with the safening agent.

The quantity of acetanilide herbicide and antagonistic agent is expressed in terms of kilograms per hectare for ease of comparing the greenhouse test results with field results. The soil containing the antagnostic agent and acetanilide herbicide is thoroughly mixed. This mixing is sometimes referred to as incorporation of the herbicide and antagonistic agent into the soil. The mixing or incorporation provides a substantially uniform distribution of the antagonistic agent and herbicide throughout the soil. The seeds are covered with the soil containing the antagonistic agent and acetanilide herbicide and the pans are leveled. The pans are then placed on a sand bench in the greenhouse and watered from below as needed. The plants are observed at the end of approximately 21 days and the results in terms of percent inhibition of each seed lot are recorded. For each test series a pan of plants is also prepared containing no acetanilide herbicide and no antagonistic agent as a control. Additionally, for each test, a pan of plants is prepared with soil covering the seed containing no acetanilide herbicide and only the measured amount of antagonistic agent being incorporated into the soil covering the seeds to ascertain any herbicidal effect of the antagonistic agent alone. For each series of tests the herbicidal effect of the acetanilide herbicide is observed from pans of plants treated with the same quantity of herbicide alone.

                                      TABLE I (A)                                  __________________________________________________________________________          Amount of                                                                      alachlor                                                                             Antag-                Per-                                          Example                                                                             Herbicide                                                                            onistic    Amount     cent In-                                                                            Safening                                 No.  (kg./ha.)                                                                            Agent      (kg./ha.)                                                                            Crop hibition                                                                            Effect (%)                               __________________________________________________________________________      1   0.14  Ethyl-N-   4.48  Wheat                                                                               10   13                                                  isopropyl-                                                                     carbamate                                                                0.14  Ethyl-N-   4.48  Sorghum                                                                              0   35                                                  isopropyl-                                                                     carbamate                                                            2   0.14  Ethyliso-  4.48  Wheat                                                                               10   13                                                  butyl-car-                                                                     bamate                                                                   0.14  Ethyliso-  4.48  Sorghum                                                                             15   20                                                  butyl-car-                                                                     bamate                                                               3   0.14  Ethyl-1,2- 4.48  Wheat                                                                                0   23                                                  dimethyl-                                                                      butylcar-                                                                      bamate                                                                   0.14  Ethyl-1,2- 4.48  Sorghum                                                                             15   20                                                  dimethyl-                                                                      butylcar-                                                                      bamate                                                               4   0.14  Ethyl-N-   4.48  Wheat                                                                                0   23                                                  ethyl,N-                                                                       t-butyl-                                                                       thiolcar-                                                                      bamate                                                                   1.12  Ethyl-N-   4.48  Wheat                                                                               10   25                                                  ethyl,N-                                                                       t-butyl-                                                                       thiolcar-                                                                      bamate                                                               5   0.14  Ethyldi-   4.48  Wheat                                                                                0   23                                                  methyl-                                                                        thionocar-                                                                     bamate                                                                   0.14  Ethyldi-   4.48  Sorghum                                                                             15   20                                                  methyl-                                                                        thionocar-                                                                     bamate                                                               6   0.14  Butylcar-  4.48  Wheat                                                                                0    5                                                  banilate                                                                 0.14  Butylcar-  4.48  Sorghum                                                                             30   35                                                  banilate                                                             7   0.14  Methyl-    4.48  Sorghum                                                                             40   25                                                  carbanilate                                                          8   0.14  Isopropyl- 4.48  Sorghum                                                                             10   55                                                  N-butyl-                                                                       carbanilate                                                              1.12  Isopropyl- 4.48  Sorghum                                                                             40   60                                                  N-butyl-                                                                       carbanilate                                                          9   0.14  Butylthiol-                                                                               2.24  Sorghum                                                                             10   55                                                  carbanilate                                                         10   0.14  Methyl-N-  4.48  Sorghum                                                                             35   30                                                  methylthiol-                                                                   carbanilate                                                              1.12  Methyl-N-  4.48  Sorghum                                                                             80   20                                                  methylthiol-                                                                   carbanilate                                                         11   1.12  Methyl-    4.48  Sorghum                                                                             75   25                                                  thiono-                                                                        carbanilate                                                         12   1.12  Methyl-2,  4.48  Sorghum                                                                             80   20                                                  6-diethyl-                                                                     thionocar-                                                                     banilate                                                            13   1.12  Allyl-N-   4.48  Sorghum                                                                             70   30                                                  ethyldithio-                                                                   carbanilate                                                         14   0.14  Butyl-N-   4.48  Sorghum                                                                             35   30                                                  ethyldithio-                                                                   carbanilate                                                              1.12  Butyl-N-   4.48  Sorghum                                                                             80   20                                                  ethyldithio-                                                                   carbanilate                                                         15   0.14  Methyl-N-  4.48  Sorghum                                                                              5   60                                                  ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N-  4.48  Sorghum                                                                             35   65                                                  ethyldithio-                                                                   carbanilate                                                         16   0.14  Hexyl-N-   4.48  Wheat                                                                                0    5                                                  ethyldithio-                                                                   carbanilate                                                              1.12  Hexyl-N-   4.48  Wheat                                                                                0   20                                                  ethyldithio-                                                                   carbanilate                                                              0.14  Hexyl-N-   4.48  Sorghum                                                                             25   40                                                  ethyldithio-                                                                   carbanilate                                                         17   0.14  Methyldi-  4.48  Sorghum                                                                             35   30                                                  thiocar-                                                                       banilate                                                            18   0.14  2-chloro-  4.48  Sorghum                                                                             35   30                                                  allyl-N-                                                                       methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  2-chloro-  4.48  Sorghum                                                                             75   25                                                  allyl-N-                                                                       methyldi-                                                                      thiocar-                                                                       banilate                                                            19   1.12  2-chloro-  4.48  Sorghum                                                                             65   35                                                  ethyl-N-                                                                       ethylthiono-                                                                   carbanilate                                                         20   0.28  Ethyl-N-   4.48  Wheat                                                                                0   30                                                  isopropyl-                                                                     carbamate                                                                0.56  Ethyl-N-   4.48  Wheat                                                                               10   30                                                  isopropyl-                                                                     carbamate                                                           21   0.28  Ethyldi-   4.48  Wheat                                                                                0   30                                                  methylthiono-                                                                  carbamate                                                                0.56  Ethyldi-   4.48  Wheat                                                                               10   30                                                  methylthiono-                                                                  carbamate                                                                1.12  Ethyldi-   4.48  Wheat                                                                               10   15                                                  methylthiono-                                                                  carbamate                                                                2.24  Ethyldi-   4.48  Wheat                                                                               20   10                                                  methylthiono-                                                                  carbamate                                                                0.28  Ethyldi-   4.48  Sorghum                                                                             45   28                                                  methylthiono-                                                                  carbamate                                                           22   0.28  Ethyliso-  4.48  Wheat                                                                                0   30                                                  butylcar-                                                                      bamate                                                                   0.56  Ethyliso-  4.48  Wheat                                                                               20   20                                                  butylcar-                                                                      bamate                                                                   1.12  Ethyliso-  4.48  Wheat                                                                               10   15                                                  butylcar-                                                                      bamate                                                                   2.24  Ethyliso-  4.48  Wheat                                                                               20   10                                                  butylcar-                                                                      bamate                                                                   0.28  Ethyliso-  4.48  Sorghum                                                                             55   18                                                  butylcar-                                                                      bamate                                                              23   0.28  Isopropyl- 4.48  Sorghum                                                                             25   48                                                  N-butylcar-                                                                    banilate                                                                 0.56  Isopropyl- 4.48  Sorghum                                                                             75   20                                                  N-butylcar-                                                                    banilate                                                                 1.12  Isopropyl- 4.48  Sorghum                                                                             60   38                                                  N-butylcar-                                                                    banilate                                                                 2.24  Isopropyl- 4.48  Sorghum                                                                             60   35                                                  N-butylcar-                                                                    banilate                                                            24   0.28  2-chloro-  4.48  Sorghum                                                                             50   23                                                  allyl-p-                                                                       methylthiol-                                                                   carbanilate                                                              0.56  2-chloro-  4.48  Sorghum                                                                             65   30                                                  allyl-p-                                                                       methylthiol-                                                                   carbanilate                                                         25   0.28  Methyl-N-  4.48  Sorghum                                                                             15   58                                                  ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N-  4.48  Sorghum                                                                             35   60                                                  ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N-  4.48  Sorghum                                                                             35   63                                                  ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N-  4.48  Sorghum                                                                             70   25                                                  ethyldithio-                                                                   carbanilate                                                         26   0.28  Hexyl-N-   4.48  Wheat                                                                               10   20                                                  ethyldithio-                                                                   carbanilate                                                              0.56  Hexyl-N-   4.48  Wheat                                                                               20   20                                                  ethyldithio-                                                                   carbanilate                                                         27   0.28  Methyl-N-  0.28  Sorghum                                                                             65   20                                                  ethyldithio-                                                                   carbanilate                                                              0.28  Methyl-N-  1.12  Sorghum                                                                             45   40                                                  ethyldithio-                                                                   carbanilate                                                              0.28  Methyl-N-  4.48  Sorghum                                                                             10   75                                                  ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N-  1.12  Sorghum                                                                             35   53                                                  ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N-  4.48  Sorghum                                                                             25   63                                                  ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N-  4.48  Sorghum                                                                             35   60                                                  ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N-  4.48  Sorghum                                                                             50   45                                                  ethyldithio-                                                                   carbanilate                                                         28   0.28  Isobutyl-N-                                                                               4.48  Sorghum                                                                             20   65                                                  butylcar-                                                                      banilate                                                                 0.56  Isobutyl-N-                                                                               4.48  Sorghum                                                                             30   58                                                  butylcar-                                                                      banilate                                                                 1.12  Isobutyl-N-                                                                               4.48  Sorghum                                                                             20   75                                                  butylcar-                                                                      banilate                                                                 2.56  Isobutyl-N-                                                                               4.48  Sorghum                                                                             65   30                                                  butylcar-                                                                      banilate                                                            29   0.28  Isobutyl-  4.48  Sorghum                                                                             15   60                                                  carbanilate                                                              0.84  Isobutyl-  4.48  Sorghum                                                                             60   30                                                  carbanilate                                                              1.12  Isobutyl-  4.48  Sorghum                                                                             65   25                                                  carbanilate                                                         30   0.28  t-butyl-   4.48  Sorghum                                                                             40   35                                                  carbanilate                                                              0.84  t-butyl-   4.48  Sorghum                                                                             70   20                                                  carbanilate                                                         31   0.28  t-butyl-   4.48  Sorghum                                                                             60   15                                                  thiolcar-                                                                      banilate                                                                 0.84  t-butyl-   4.48  Sorghum                                                                             75   15                                                  thiolcar-                                                                      banilate                                                            32   0.28  Sec-butyl- 4.48  Sorghum                                                                             55   20                                                  N-ethyldi-                                                                     thiocar-                                                                       banilate                                                            33   2.24  Ethyl-N-   4.48  Wheat                                                                               30   45                                                  ethyldithio-                                                                   carbanilate                                                              0.28  Ethyl-N-   4.48  Sorghum                                                                             35   53                                                  ethyldithio-                                                                   carbanilate                                                              0.84  Ethyl-N-   4.48  Sorghum                                                                             40   53                                                  ethyldithio-                                                                   carbanilate                                                              2.24  Ethyl-N-   4.48  Sorghum                                                                             75   23                                                  ethyldithio-                                                                   carbanilate                                                         34   2.24  Propyl-N-  4.48  Wheat                                                                               15   60                                                  ethyldithio-                                                                   carbanilate                                                              0.28  Propyl-N-  4.48  Sorghum                                                                             45   43                                                  ethyldithio-                                                                   carbanilate                                                         35   2.24  Butyldithio-                                                                              2.24  Wheat                                                                               35   40                                                  carbanilate                                                              0.28  Butyldithio-                                                                              2.24  Sorghum                                                                             60   28                                                  carbanilate                                                         36   0.28  Methyl-N-  2.24  Sorghum                                                                             50   38                                                  isopropyl-                                                                     thiolcar-                                                                      banilate                                                                 0.84  Methyl-N-  2.24  Sorghum                                                                             70   23                                                  isopropyl-                                                                     thiolcar-                                                                      banilate                                                            37   0.28  Isopropyl- 0.56  Sorghum                                                                             75   13                                                  N-propyl-                                                                      thiolcar-                                                                      banilate                                                                 0.84  Isopropyl- 0.56  Sorghum                                                                             75   18                                                  N-propyl-                                                                      thiolcar-                                                                      banilate                                                            38   0.28  t-butyl-   4.48  Sorghum                                                                             40   48                                                  N-isopropyl-                                                                   thiolcar-                                                                      banilate                                                                 0.84  t-butyl-   4.48  Sorghum                                                                             60   33                                                  N-isopropyl-                                                                   thiolcar-                                                                      banilate                                                                 2.24  t-butyl-   4.48  Sorghum                                                                             70   28                                                  N-isopropyl-                                                                   thiolcar-                                                                      banilate                                                            39   0.28  Ethyl-N-t- 4.48  Sorghum                                                                             45   43                                                  butylcar-                                                                      banilate                                                                 0.84  Ethyl-N-t- 4.48  Sorghum                                                                             75   18                                                  butylcar-                                                                      banilate                                                            40   2.24  Propyl-N-  4.48  Sorghum                                                                             50   25                                                  isopropyl-                                                                     dithiocar-                                                                     banilate                                                            41   0.28  Allylthiono-                                                                              4.48  Wheat                                                                                0   20                                                  carbanilate                                                              0.84  Allylthiono-                                                                              4.48  Wheat                                                                                0   65                                                  carbanilate                                                              2.24  Allylthiono-                                                                              4.48  Wheat                                                                                0   70                                                  carbanilate                                                              0.28  Allylthiono-                                                                              4.48  Sorghum                                                                             20   30                                                  carbanilate                                                              0.84  Allylthiono-                                                                              4.48  Sorghum                                                                             40   55                                                  carbanilate                                                              2.24  Allylthiono-                                                                              4.48  Sorghum                                                                             75   19                                                  carbanilate                                                         42   0.28  2-methyl-  4.48  Wheat                                                                                0   20                                                  allylcar-                                                                      banilate                                                                 2.24  2-methyl-  4.48  Wheat                                                                               50   20                                                  allylcar-                                                                      banilate                                                                 0.28  2-methyl-  4.48  Sorghum                                                                             25   25                                                  allylcar-                                                                      banilate                                                                 0.84  2-methyl-  4.48  Sorghum                                                                             45   50                                                  allylcar-                                                                      banilate                                                                 2.24  2-methyl-  4.48  Sorghum                                                                             70   24                                                  allylcar-                                                                      banilate                                                            43   2.24  Allyl-N-   4.48  Wheat                                                                               30   40                                                  methylcar-                                                                     banilate                                                                 0.28  Allyl-N-   4.48  Sorghum                                                                             15   35                                                  methylcar-                                                                     banilate                                                                 0.84  Allyl-N-   4.48  Sorghum                                                                             65   30                                                  methylcar-                                                                     banilate                                                                 2.24  Allyl-N-   4.48  Sorghum                                                                             85    9                                                  methylcar-                                                                     banilate                                                            44   0.84  Pentyl-3,  4.48  Wheat                                                                                0    5                                                  4-dichloro-                                                                    thionocar-                                                                     banilate                                                                 2.24  Pentyl-3,  4.48  Wheat                                                                                0   20                                                  4-dichloro-                                                                    thionocar-                                                                     banilate                                                            45   0.28  Ethyl-3,4- 4.48  Sorghum                                                                             35   54                                                  dichlorothiol-                                                                 carbanilate                                                         46   0.28  Methyl-p-  2.24  Wheat                                                                                0    5                                                  chlorothiono-                                                                  carbanilate                                                              0.84  Methyl-p-  2.24  Wheat                                                                                0    5                                                  chlorothiono-                                                                  carbanilate                                                              2.24  Methyl-p-  2.24  Wheat                                                                                0   20                                                  chlorothiono-                                                                  carbanilate                                                         47   0.28  2-chloro-  4.48  Sorghum                                                                             60   29                                                  allyl-p-methyl-                                                                thiolcarbanilate                                                    48   0.28  2-chloro-  4.48  Sorghum                                                                             30   59                                                  allyl-N-methyl-                                                                dithiocar-                                                                     banilate                                                                 0.84  2-chloro-  4.48  Sorghum                                                                             35   53                                                  allyl-N-methyl-                                                                dithiocar-                                                                     banilate                                                                 2.24  2-chloro-  4.48  Sorghum                                                                             60   37                                                  allyl-N-methyl-                                                                dithiocar-                                                                     banilate                                                            49   0.28  Hexyl-m-   4.48  Sorghum                                                                             65   24                                                  methylcar-                                                                     banilate                                                            50   0.28  2-chloro-  4.48  Sorghum                                                                             60   29                                                  allyl-N-                                                                       propyldithio-                                                                  carbanilate                                                         51   0.28  2-chloro-  4.48  Sorghum                                                                             30   59                                                  allyl-N-iso-                                                                   propyldithio-                                                                  carbanilate                                                         52   0.28  Allyl-N-   4.48  Sorghum                                                                             10   79                                                  methyldithio-                                                                  carbanilate                                                              0.84  Allyl-N-   4.48  Sorghum                                                                             15   73                                                  methyldithio-                                                                  carbanilate                                                              2.24  Allyl-N-   4.48  Sorghum                                                                             30   67                                                  methyldithio-                                                                  carbanilate                                                         53   0.28  Butyl-3,4- 4.48  Sorghum                                                                             50   29                                                  dichloro-                                                                      thiolcar-                                                                      banilate                                                            54   0.28  Allyl-N-   4.48  Sorghum                                                                             50   20                                                  ethyldithio-                                                                   carbanilate                                                              0.84  Allyl-N-   4.48  Sorghum                                                                             75   23                                                  ethyldithio-                                                                   carbanilate                                                         55   0.28  2-chloro-  4.48  Sorghum                                                                             40   15                                                  ethyl-N-                                                                       methylthiono-                                                                  carbanilate                                                         56   0.28  2-chloro-  4.48  Wheat                                                                                0   80                                                  allyl-o-chloro-                                                                N-(2-chloroallyl)                                                              dithiocarbanilate                                                        0.28  2-chloro-  4.48  Sorghum                                                                             15   40                                                  allyl-o-chloro-                                                                N-(2-chloroallyl)                                                              dithiocarbanilate                                                        0.84  2-chloro-  4.48  Sorghum                                                                             50   35                                                  allyl-o-chloro-                                                                N-(2-chloroallyl)                                                              dithiocarbanilate                                                   57   0.84  Ethyl-N-   4.48  Sorghum                                                                             60   25                                                  (2-carbamoylethyl)-                                                            thiolcarbanilate                                                         2.24  Ethyl-N-   4.48  Sorghum                                                                             70   28                                                  (2-carbamoylethyl)-                                                            thiolcarbanilate                                                    58   0.28  Allyldi-   4.48  Wheat                                                                               20   18                                                  thiocarbanilate                                                          0.28  Allyldi-   4.48  Sorghum                                                                             50   10                                                  thiocarbanilate                                                          0.84  Allyldi-   4.48  Sorghum                                                                             65   23                                                  thiocarbanilate                                                     59   0.28  Methyl-p-  4.48  Wheat                                                                               20   18                                                  t-butyl-                                                                       thionocar-                                                                     banilate                                                                 0.28  Methyl-p-  4.48  Sorghum                                                                             25   35                                                  t-butyl-                                                                       thionocar-                                                                     banilate                                                                 0.84  Methyl-p-  4.48  Sorghum                                                                             55   33                                                  t-butyl-                                                                       thionocar-                                                                     banilate                                                                 2.24  Methyl-p-  4.48  Sorghum                                                                             85   8                                                   t-butyl-                                                                       thionocar-                                                                     banilate                                                            60   0.28  Ethyl-3-   4.48  Wheat                                                                               20   18                                                  hydroxy-N-                                                                     isopropyl-                                                                     thiolcar-                                                                      banilate                                                                 0.28  Ethyl-3-   4.48  Sorghum                                                                             45   15                                                  hydroxy-N-                                                                     isopropyl-                                                                     thiolcar-                                                                      banilate                                                                 0.84  Ethyl-3-   4.48  Sorghum                                                                             75   13                                                  hydroxy-N-                                                                     isopropyl-                                                                     thiolcar-                                                                      banilate                                                            61   0.28  Isopropyl- 4.48  Sorghum                                                                             40   30                                                  N-butyl-                                                                       carbanilate                                                              0.56  Isopropyl- 4.48  Sorghum                                                                             55   33                                                  N-butyl-                                                                       carbanilate                                                              1.12  Isopropyl- 4.48  Sorghum                                                                             55   38                                                  N-butyl-                                                                       carbanilate                                                              2.24  Isopropyl- 4.48  Sorghum                                                                             55   43                                                  N-butyl-                                                                       carbanilate                                                         62   0.28  Methyl-N-  4.48  Sorghum                                                                             50   20                                                  ethyldi-                                                                       thiocar-                                                                       banilate                                                                 0.56  Methyl-N-  4.48  Sorghum                                                                             50   38                                                  ethyldi-                                                                       thiocar-                                                                       banilate                                                                 1.12  Methyl-N-  4.48  Sorghum                                                                             70   23                                                  ethyldi-                                                                       thiocar-                                                                       banilate                                                                 2.24  Methyl-N-  4.48  Sorghum                                                                             90    8                                                  ethyldi-                                                                       thiocar-                                                                       banilate                                                            63   0.28  Isobutyl-  4.48  Sorghum                                                                             30   40                                                  carbanilate                                                              0.56  Isobutyl-  4.48  Sorghum                                                                             70   18                                                  carbanilate                                                              1.12  Isobutyl-  4.48  Sorghum                                                                             70   23                                                  carbanilate                                                              2.24  Isobutyl-  4.48  Sorghum                                                                             70   28                                                  carbanilate                                                         64   0.28  t-butyl-   4.48  Sorghum                                                                             55   15                                                  carbanilate                                                              0.56  t-butyl-   4.48  Sorghum                                                                             75   13                                                  carbanilate                                                              1.12  t-butyl-   4.48  Sorghum                                                                             80   13                                                  carbanilate                                                              2.24  t-butyl-   4.48  Sorghum                                                                             85   13                                                  carbanilate                                                         65   0.28  Ethyl-N-   4.48  Sorghum                                                                             45   25                                                  ethyldithio-                                                                   carbanilate                                                              0.56  Ethyl-N-   4.48  Sorghum                                                                             60   28                                                  ethyldithio-                                                                   carbanilate                                                              1.12  Ethyl-N-   4.48  Sorghum                                                                             70   23                                                  ethyldithio-                                                                   carbanilate                                                              2.24  Ethyl-N-   4.48  Sorghum                                                                             70   28                                                  ethyldithio-                                                                   carbanilate                                                         66   0.56  t-butyl-N- 4.48  Sorghum                                                                             50   38                                                  isopropyl-                                                                     thiolcar-                                                                      banilate                                                                 1.12  t-butyl-N- 4.48  Sorghum                                                                             65   28                                                  isopropyl-                                                                     thiolcar-                                                                      banilate                                                            67   0.28  Allyl-     4.48  Sorghum                                                                             45   25                                                  thionocar-                                                                     banilate                                                                 0.56  Allyl-     4.48  Sorghum                                                                             65   23                                                  thionocar-                                                                     banilate                                                                 1.12  Allyl-     4.48  Sorghum                                                                             65   28                                                  thionocar-                                                                     banilate                                                                 2.24  Allyl-     4.48  Sorghum                                                                             75   23                                                  thionocar-                                                                     banilate                                                            68   0.28  2-methyl-  4.48  Sorghum                                                                             50   20                                                  allylcar-                                                                      banilate                                                                 0.56  2-methyl-  4.48  Sorghum                                                                             65   23                                                  allylcar-                                                                      banilate                                                                 1.12  2-methyl-  4.48  Sorghum                                                                             60   33                                                  allylcar-                                                                      banilate                                                                 2.24  2-methyl-  4.48  Sorghum                                                                             70   28                                                  allylcar-                                                                      banilate                                                            69   0.28  Allyl-N-   2.24  Sorghum                                                                             35   35                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.28  Allyl-N-   4.48  Sorghum                                                                             30   40                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.56  Allyl-N-   2.24  Sorghum                                                                             55   33                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.56  Allyl-N-   4.48  Sorghum                                                                             35   53                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  Allyl-N-   2.24  Sorghum                                                                             60   33                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  Allyl-N-   4.48  Sorghum                                                                             45   48                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 2.24  Allyl-N-   2.24  Sorghum                                                                             80   18                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 2.24  Allyl-N-   4.48  Sorghum                                                                             55   43                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                            70   0.28  Ethyl-3,4- 4.48  Sorghum                                                                             55   15                                                  dichloro-                                                                      thiolcar-                                                                      banilate                                                                 0.56  Ethyl-3,4- 4.48  Sorghum                                                                             65   23                                                  dichloro-                                                                      thiolcar-                                                                      banilate                                                            71   0.28  2-chloro-  4.48  Sorghum                                                                             45   25                                                  allyl-N-                                                                       methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.56  2-chloro-  4.48  Sorghum                                                                             60   28                                                  allyl-N-                                                                       methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  2-chloro-  4.48  Sorghum                                                                             70   23                                                  allyl-N-                                                                       methyldi-                                                                      thiocar-                                                                       banilate                                                                 2.24  2-chloro-  4.48  Sorghum                                                                             80   18                                                  allyl-N-                                                                       methyldi-                                                                      thiocar-                                                                       banilate                                                            72   0.28  2-chloro-  4.48  Sorghum                                                                             50   20                                                  allyl-o-                                                                       chloro-N-                                                                      (2-chloroallyl)                                                                dithiocar-                                                                     banilate                                                                 0.56  2-chloro-  4.48  Sorghum                                                                             70   18                                                  allyl-o-                                                                       chloro-N-                                                                      (2-chloroallyl)                                                                dithiocar-                                                                     banilate                                                            73   0.28  Methyl-p-  4.48  Sorghum                                                                             35   35                                                  t-butyl-                                                                       thionocar-                                                                     banilate                                                                 0.56  Methyl-p-  4.48  Sorghum                                                                             60   28                                                  t-butyl-                                                                       thionocar-                                                                     banilate                                                                 1.12  Methyl-p-  4.48  Sorghum                                                                             70   23                                                  t-butyl-                                                                       thionocar-                                                                     banilate                                                                 2.24  Methyl-p-  4.48  Sorghum                                                                             75   23                                                  t-butyl-                                                                       thionocar-                                                                     banilate                                                            74   0.28  Cyclohexyl-                                                                               4.48  Sorghum                                                                             50   49                                                  N-allyl-cyclo-                                                                 hexanecarbamate                                                     75   2.24  Cyclo-     4.48  Wheat                                                                               60   20                                                  hexyldi-                                                                       ethyldithio-                                                                   carbamate                                                           76   0.28  Isopropyl- 4.48  Wheat                                                                               60   20                                                  N-ethylcyclo-                                                                  hexanecar-                                                                     bamate                                                                   2.24  Isopropyl- 4.48  Sorghum                                                                             75   24                                                  N-ethylcyclo-                                                                  hexanecar-                                                                     bamate                                                              77   0.28  Methyl-N-  4.48  Sorghum                                                                             60   39                                                  isopropyldi-                                                                   thiocyclo-                                                                     hexanecar-                                                                     bamate                                                              78   2.24  Methyl-N-  4.48  Wheat                                                                               50   30                                                  methylthiono-                                                                  cyclohexane-                                                                   carbamate                                                                0.28  Methyl-N-  4.48  Sorghum                                                                             80   19                                                  methylthiono-                                                                  cyclohexane-                                                                   carbamate                                                           79   0.28  Ethyl-N-   4.48  Sorghum                                                                             75   24                                                  methylthiono-                                                                  cyclohexane-                                                                   carbamate                                                           80   0.28  Ethyl-N-   4.48  Sorghum                                                                             60   39                                                  ethylthiono-                                                                   cyclohexane-                                                                   carbamate                                                           81   2.24  Propyl-N-  4.48  Wheat                                                                               40   40                                                  butylthiono-                                                                   cyclohexane-                                                                   carbamate                                                           82   0.28  Phenyldi-  4.48  Sorghum                                                                             65   33                                                  ethyldithio-                                                                   carbamate                                                           83   0.28  Ethyl-     4.48  Sorghum                                                                             75   23                                                  pyrrolidine-                                                                   thionocarboxy-                                                                 late                                                                84   0.28  2-chloro-  4.48  Sorghum                                                                             75   22                                                  allyl-3,6-                                                                     dihydro-1(2H)                                                                  pyridinecar-                                                                   bodithioate                                                              2.24  2-chloro-  4.48  Sorghum                                                                             70   30                                                  allyl-3,6-                                                                     dihydro-1(2H)                                                                  pyridinecar-                                                                   bodithioate                                                         85   0.28  2-chloro-  4.48  Sorghum                                                                             75   22                                                  allyl-3,6-                                                                     dihydro-1(2H)                                                                  pyridinecar-                                                                   bothiolate                                                               2.24  2-chloro-  4.48  Sorghum                                                                             65   35                                                  allyl-3,6-                                                                     dihydro-1(2H)                                                                  pyridinecar-                                                                   bothiolate                                                          86   0.28  2-hydroxy- 4.48  Sorghum                                                                             75   22                                                  ethyl-5-ethyl-                                                                 2-methyl-1-                                                                    piperidinecarbo-                                                               dithioate                                                           87   0.28  Ethyl-     4.48  Wheat                                                                               10   15                                                  piperidinethio-                                                                carboxylate                                                              2.24  Ethyl-     4.48  Wheat                                                                               60   20                                                  piperidinethio-                                                                carboxylate                                                              0.28  Ethyl-     4.48  Sorghum                                                                             80   17                                                  piperidinethio-                                                                carboxylate                                                         88   2.24  2-cyclo-   4.48  Wheat                                                                               35   25                                                  hexen-1-yldiiso-                                                               propylthiolcar-                                                                bamate                                                              89   0.28  Allyldithio-                                                                              4.48  Wheat                                                                                0   10                                                  2-cyclohexene-                                                                 1-carbamate                                                              2.24  Allyldithio-                                                                              4.48  Wheat                                                                               35   25                                                  2-cyclohexene-                                                                 1-carbamate                                                         90   0.28  Methyl-    4.48  Sorghum                                                                             60   35                                                  N-isopropyl-                                                                   thiol-2-cyclo-                                                                 hexene-1-car-                                                                  bamate                                                              91   0.28  Ethyl-4-   4.48  Wheat                                                                               20   30                                                  morpholine-                                                                    carbothionate                                                            2.24  Ethyl-4-   4.48  Wheat                                                                               75   23                                                  morpholine-                                                                    carbothionate                                                       92   0.28  3-chloro-  4.48  Wheat                                                                               25   25                                                  2-butyl-4-                                                                     morpholine-                                                                    carbodithioate                                                           2.24  3-chloro-  4.48  Wheat                                                                               80    8                                                  2-butyl-4-                                                                     morpholine-                                                                    cardodithioate                                                      93   0.28  Allyl-4-   4.48  Wheat                                                                               20   30                                                  morpholinecarbo-                                                               thionate                                                                 2.24  Allyl-4-   4.48  Wheat                                                                               80    8                                                  morpholinecarbo-                                                               thionate                                                            94   0.28  2-chloro-  4.48  Wheat                                                                               30   20                                                  allyl-2,6-di-                                                                  methyl-4-                                                                      morpholinecar-                                                                 bodithioate                                                              0.28  2-chloro-  4.48  Sorghum                                                                             75   22                                                  allyl-2,6-di-                                                                  methyl-4-                                                                      morpholinecar-                                                                 bodithioate                                                         95   0.28  Ethylhexa- 4.48  Wheat                                                                               20   30                                                  hydro(1H)azepine-                                                              1-carbothionate                                                          2.24  Ethylhexa- 4.48  Wheat                                                                               75   13                                                  hydro(1H)azepine-                                                              1-carbothionate                                                     96   0.28  Methylhexa-                                                                               4.48  Wheat                                                                               25   25                                                  hydro(1H)azepine-                                                              1-carboxylate                                                       97   0.28  Pentylhexa-                                                                               4.48  Wheat                                                                               15   35                                                  hydro(1H)azepine-                                                              1-carboxylate                                                            2.24  Pentylhexa-                                                                               4.48  Wheat                                                                               70   18                                                  hydro(1H)azepine-                                                              1-carboxylate                                                            0.28  Pentylhexa-                                                                               4.48  Sorghum                                                                             70   27                                                  hydro(1H)azepine-                                                              1-carboxylate                                                       98   0.28  Isopropyl- 4.48  Wheat                                                                               20   30                                                  hexahydro(1H)                                                                  azepine-1-                                                                     carboxylate                                                              2.24  Isopropyl- 4.48  Wheat                                                                               80    8                                                  hexahydro(1H)                                                                  azepine-1-                                                                     carboxylate                                                         99   0.28  Octylocta- 1.12  Wheat                                                                               30   20                                                  hydro(1H)azonine-                                                              1-carbothiolate                                                          2.24  Octylocta- 1.12  Wheat                                                                               75   13                                                  hydro(1H)azonine-                                                              1-carbothiolate                                                     100  0.28  Isopropyl- 4.48  Wheat                                                                               30   20                                                  hexahydroazocine-                                                              1(2H)azoninethiono-                                                            carboxylate                                                              2.24  Isopropyl- 4.48  Wheat                                                                               65   23                                                  hexahydroazocine-                                                              1(2H)azoninethiono-                                                            carboxylate                                                         101  0.28  Ethylocta- 4.48  Wheat                                                                               20   30                                                  hydro(1H)azonine-                                                              thionocarboxylate                                                        2.24  Ethylocta- 4.48  Wheat                                                                               60   28                                                  hydro(1H)azonine-                                                              thionocarboxylate                                                   102  0.07  Allyl-N-   4.48  Wheat                                                                                0   10                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.28  Allyl-N-   4.48  Wheat                                                                               15   23                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  Allyl-N-   4.48  Wheat                                                                               35   40                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.07  Allyl-N-   4.48  Sorghum                                                                             15   35                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.28  Allyl-N-   4.48  Sorghum                                                                             40   58                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  Allyl-N-   4.48  Sorghum                                                                             80   20                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                            103  0.07  Methyl-N-  4.48  Wheat                                                                                0   10                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.28  Methyl-N-  4.48  Wheat                                                                                0   38                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  Methyl-N-  4.48  Wheat                                                                               20   55                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 4.48  Methyl-N-  4.48  Wheat                                                                               40   50                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.07  Methyl-N-  4.48  Sorghum                                                                             20   30                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.28  Methyl-N-  4.48  Sorghum                                                                             50   48                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  Methyl-N-  4.48  Sorghum                                                                             85   15                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                            104  0.07  Butyl-N-   4.48  Wheat                                                                                0   10                                                  methylcar-                                                                     banilate                                                                 0.28  Butyl-N-   4.48  Wheat                                                                               15   23                                                  methylcar-                                                                     banilate                                                                 1.12  Butyl-N-   4.48  Wheat                                                                               40   35                                                  methylcar-                                                                     banilate                                                                 0.07  Butyl-N-   4.48  Sorghum                                                                             25   25                                                  methylcar-                                                                     banilate                                                                 0.28  Butyl-N-   4.48  Sorghum                                                                             75   23                                                  methylcar-                                                                     banilate                                                            105  0.14  2-chloro-  4.48  Wheat                                                                                0   20                                                  allyl-3,4-di-                                                                  chloro-N-(2-                                                                   chloroallyl)                                                                   dithiocar-                                                                     banilate                                                                 0.84  2-chloro-  4.48  Wheat                                                                               45   40                                                  allyl-3,4-di-                                                                  chloro-N-(2-                                                                   chloroallyl)                                                                   dithiocar-                                                                     banilate                                                                 0.14  2-chloro-  4.48  Sorghum                                                                             50   40                                                  allyl-3,4-di-                                                                  chloro-N-(2-                                                                   chloroallyl)                                                                   dithiocar-                                                                     banilate                                                            106  0.14  2-chloro-  4.48  Sorghum                                                                             50   40                                                  allyl-N-allyl-3,4-                                                             dichlorodithio-                                                                carbanilate                                                         107  0.14  Methyl-N-  4.48  Wheat                                                                                0   20                                                  allyl-3,4-                                                                     dichlorodithio-                                                                carbanilate                                                              0.14  Methyl-N-  4.48  Sorghum                                                                             65   25                                                  allyl-3,4-                                                                     dichlorodithio-                                                                carbanilate                                                         108  0.14  Allyl-3,4- 4.48  Wheat                                                                               10   10                                                  dichloro-N-                                                                    (2-chloroallyl)                                                                dithiocarbanilate                                                        0.84  Allyl-3,4- 4.48  Wheat                                                                               70   15                                                  dichloro-N-                                                                    (2-chloroallyl)                                                                dithiocarbanilate                                                        0.14  Allyl-3,4- 4.48  Sorghum                                                                             65   25                                                  dichloro-N-                                                                    (2-chloroallyl)                                                                dithiocarbanilate                                                   109  0.14  2-chloro-  4.48  Sorghum                                                                             75   15                                                  allyl-p-chloro-                                                                N-ethyldithio-                                                                 carbanilate                                                         110  0.14  2,3,3-tri- 4.48  Sorghum                                                                             60   30                                                  chloroallyl-o-                                                                 chlorocarbanilate                                                   111  0.14  2,3,3-tri- 4.48  Sorghum                                                                             70   20                                                  chloroallyl-p-                                                                 chlorocarbanilate                                                   112  0.14  2-chloro-3-                                                                               4.48  Wheat                                                                               10   50                                                  butenyl-p-bromo-                                                               carbanilate                                                              0.84  2-chloro-3-                                                                               4.48  Wheat                                                                               70   24                                                  butenyl-p-bromo-                                                               carbanilate                                                              0.14  2-chloro-3-                                                                               4.48  Sorghum                                                                             65   25                                                  butenyl-p-bromo-                                                               carbanilate                                                         113  0.14  Allyl-p-   4.48  Wheat                                                                               35   25                                                  chlorodi-                                                                      thiocar-                                                                       banilate                                                                 0.84  Allyl-p-   4.48  Wheat                                                                               70   24                                                  chlorodi-                                                                      thiocar-                                                                       banilate                                                                 0.14  Allyl-p-   4.48  Sorghum                                                                             65   24                                                  chlorodi-                                                                      thiocar-                                                                       banilate                                                            114  0.14  2-chloro-  4.48  Wheat                                                                                0   60                                                  allyl-p-                                                                       chlorodi-                                                                      thiocar-                                                                       banilate                                                                 0.84  2-chloro-  4.48  Wheat                                                                               55   39                                                  allyl-p-                                                                       chlorodi-                                                                      thiocar-                                                                       banilate                                                            115  0.14  2-chloro-  4.48  Wheat                                                                               25   35                                                  allyl-3,4-di-                                                                  chlorodithio-                                                                  carbanilate                                                         116  0.14  2-chloro-  4.48  Wheat                                                                               30   30                                                  allyl-p-nitro-                                                                 dithiocarbanilate                                                        0.84  2-chloro-  4.48  Wheat                                                                               75   19                                                  allyl-p-nitro-                                                                 dithiocarbanilate                                                   117  0.14  2-chloro-  4.48  Wheat                                                                               25   35                                                  allyl-3-nitro-                                                                 carbanilate                                                         118  0.14  3-chloro-  4.48  Wheat                                                                               35   25                                                  allyl-3-nitro-                                                                 carbanilate                                                              0.14  3-chloro-  4.48  Sorghum                                                                             75   15                                                  allyl-3-nitro-                                                                 carbanilate                                                         119  0.14  2-chloro-  4.48  Wheat                                                                               10   50                                                  allyl-p-fluoro-                                                                dithiocarbanilate                                                        0.84  2-chloro-  4.48  Wheat                                                                               70   24                                                  allyl-p-fluoro-                                                                dithiocarbanilate                                                   120  0.14  4-iodo-2-  4.48  Wheat                                                                               15   35                                                  butynyl-p-                                                                     methoxycar-                                                                    banilate                                                                 0.84  4-iodo-2-  4.48  Wheat                                                                               50   44                                                  butynyl-p-                                                                     methoxycar-                                                                    banilate                                                                 4.48  4-iodo-2-  4.48  Wheat                                                                               75   20                                                  butynyl-p-                                                                     methoxycar-                                                                    banilate                                                                 0.14  4-iodo-2-  4.48  Sorghum                                                                             75   15                                                  butynyl-p-                                                                     methoxycar-                                                                    banilate                                                            121  0.07  Allyl-N-   4.48  Wheat                                                                                0   30                                                  methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-   4.48  Wheat                                                                               10   25                                                  methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-   4.48  Wheat                                                                               30   35                                                  methyldithio-                                                                  carbanilate                                                              0.07  Allyl-N-   4.48  Sorghum                                                                             15   80                                                  methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-   4.48  Sorghum                                                                             30   65                                                  methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-   4.48  Sorghum                                                                             50   49                                                  methyldithio-                                                                  carbanilate                                                              4.48  Allyl-N-   4.48  Sorghum                                                                             75   24                                                  methyldithio-                                                                  carbanilate                                                         122  0.07  Benzyldi-  4.48  Wheat                                                                                0   30                                                  isopropylcar-                                                                  bamate                                                                   0.28  Benzyldi-  4.48  Wheat                                                                               20   15                                                  isopropylcar-                                                                  bamate                                                                   1.12  Benzyldi-  4.48  Wheat                                                                               35   30                                                  isopropylcar-                                                                  bamate                                                                   4.48  Benzyldi-  4.48  Wheat                                                                               80   18                                                  isopropylcar-                                                                  bamate                                                                   0.07  Benzyldi-  4.48  Sorghum                                                                             20   75                                                  isopropylcar-                                                                  bamate                                                                   0.28  Benzyldi-  4.48  Sorghum                                                                             40   55                                                  isopropylcar-                                                                  bamate                                                                   1.12  Benzyldi-  4.48  Sorghum                                                                             65   34                                                  isopropylcar-                                                                  bamate                                                              123  0.07  Benzyliso- 2.24  Wheat                                                                                0   30                                                  butyldithio-                                                                   carbamate                                                                0.28  Benzyliso- 2.24  Wheat                                                                               10   25                                                  butyldithio-                                                                   carbamate                                                                1.12  Benzyliso- 2.24  Wheat                                                                               45   20                                                  butyldithio-                                                                   carbamate                                                                4.48  Benzyliso- 2.24  Wheat                                                                               75   23                                                  butyldithio-                                                                   carbamate                                                                0.07  Benzyliso- 2.24  Sorghum                                                                             55   40                                                  butyldithio-                                                                   carbamate                                                                0.28  Benzyliso- 2.24  Sorghum                                                                             70   25                                                  butyldithio-                                                                   carbamate                                                           124  0.07  Cyclo-     4.48  Wheat                                                                                0   30                                                  hexyl-N-allyl-                                                                 cyclohexane-                                                                   carbamate                                                                0.28  Cyclo-     4.48  Wheat                                                                               15   20                                                  hexyl-N-allyl-                                                                 cyclohexane-                                                                   carbamate                                                                0.07  Cyclo-     4.48  Sorghum                                                                             30   65                                                  hexyl-N-allyl-                                                                 cyclohexane-                                                                   carbamate                                                                0.28  Cyclo-     4.48  Sorghum                                                                             70   25                                                  hexyl-N-allyl-                                                                 cyclohexane-                                                                   carbamate                                                           125  0.07  Ethyl-N-   2.24  Wheat                                                                                0   30                                                  ethylthiono-                                                                   cyclohexane-                                                                   carbamate                                                                0.28  Ethyl-N-   2.24  Wheat                                                                               10   25                                                  ethylthiono-                                                                   cyclohexane-                                                                   carbamate                                                                0.07  Ethyl-N-   2.24  Sorghum                                                                             30   65                                                  ethylthiono-                                                                   cyclohexane-                                                                   carbamate                                                                0.28  Ethyl-N-   2.24  Sorghum                                                                             70   25                                                  ethylthiono-                                                                   cyclohexane-                                                                   carbamate                                                           126  0.07  Ethylthiol-                                                                               4.48  Wheat                                                                                0   30                                                  cyclohexane-                                                                   carbamate                                                                0.07  Ethylthiol-                                                                               4.48  Sorghum                                                                             40   55                                                  cyclohexane-                                                                   carbamate                                                           127  0.07  Propyl-N-  4.48  Wheat                                                                                0   30                                                  butylthiono-                                                                   cyclohexane-                                                                   carbamate                                                                0.28  Propyl-N-  4.48  Wheat                                                                               15   20                                                  butylthiono-                                                                   cyclohexane-                                                                   carbamate                                                                0.07  Propyl-N-  4.48  Sorghum                                                                             70   25                                                  butylthiono-                                                                   cyclohexane-                                                                   carbamate                                                           128  0.07  Phenyldi-  4.48  Wheat                                                                                0   30                                                  ethyldithio-                                                                   carbamate                                                                0.28  Phenyldi-  4.48  Wheat                                                                               10   25                                                  ethyldithio-                                                                   carbamate                                                                0.07  Phenyldi-  4.48  Sorghum                                                                              0   95                                                  ethyldithio-                                                                   carbamate                                                                0.28  Phenyldi-  4.48  Sorghum                                                                             40   55                                                  ethyldithio-                                                                   carbamate                                                           129  0.07  2-chloro-  4.48  Wheat                                                                                0   30                                                  allyl-3,6-dihydro-                                                             1(2H)pyridine carbo-                                                           thiolate                                                                 0.07  2-chloro-  4.48  Sorghum                                                                             60   35                                                  allyl-3,6-dihydro-                                                             1(2H)pyridine carbo-                                                           thiolate                                                            130  0.07  Ethyl-     4.48  Wheat                                                                                0   30                                                  piperidinethio-                                                                carboxylate                                                              0.28  Ethyl-     4.48  Wheat                                                                               20   15                                                  piperidinethio-                                                                carboxylate                                                              1.12  Ethyl-     4.48  Wheat                                                                               45   20                                                  piperidinethio-                                                                carboxylate                                                              0.07  Ethyl-     4.48  Sorghum                                                                             75   20                                                  piperidinethio-                                                                carboxylate                                                         131  0.28  Allyl-N-   4.48  Wheat                                                                                0   25                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  Allyl-N-   4.48  Wheat                                                                               45   25                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.07  Allyl-N-   4.48  Sorghum                                                                             15   35                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 0.28  Allyl-N-   4.48  Sorghum                                                                             25   65                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 1.12  Allyl-N-   4.48  Sorghum                                                                             40   60                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                                 4.48  Allyl-N-   4.48  Sorghum                                                                             50   50                                                  methyldi-                                                                      thiocar-                                                                       banilate                                                            132  0.07  Allyldi-   4.48  Sorghum                                                                             25   25                                                  thio-2-cyclo-                                                                  hexene-1-car-                                                                  bamate                                                                   0.28  Allyldi-   4.48  Sorghum                                                                             50   40                                                  thio-2-cyclo-                                                                  hexene-1-car-                                                                  bamate                                                                   1.12  Allyldi-   4.48  Sorghum                                                                             80   20                                                  thio-2-cyclo-                                                                  hexene-1-car-                                                                  bamate                                                              133  0.28  2-cyclo-   4.48  Wheat                                                                               10   15                                                  hexen-1-yl                                                                     diisopropyl-                                                                   thiolcarbamate                                                           1.12  2-cyclo-   4.48  Wheat                                                                               20   50                                                  hexen-1-yl                                                                     diisopropyl-                                                                   thiolcarbamate                                                      134  0.07  Pentylhexa-                                                                               4.48  Sorghum                                                                             25   24                                                  hydro(1H)-                                                                     azepine-1-car-                                                                 boxylate                                                                 0.28  Pentylhexa-                                                                               4.48  Sorghum                                                                             50   40                                                  hydro(1H)-                                                                     azepine-1-car-                                                                 boxylate                                                                 1.12  Pentylhexa-                                                                               4.48  Sorghum                                                                             85   15                                                  hydro(1H)-                                                                     azepine-1-car-                                                                 boxylate                                                            135  0.28  Isopropyl- 4.48  Wheat                                                                                0   25                                                  hexahydroazocine-                                                              1(2H)carbothionate                                                       1.12  Isopropyl- 4.48  Wheat                                                                               25   45                                                  hexahydroazocine-                                                              1(2H)carbothionate                                                       4.48  Isopropyl- 4.48  Wheat                                                                               75   15                                                  hexahydroazocine-                                                              1(2H)carbothionate                                                  136  0.28  Ethylocta- 4.48  Wheat                                                                                0   25                                                  hydro(1H)azonine-                                                              thionocarboxylate                                                        1.12  Ethylocta- 4.48  Wheat                                                                               30   40                                                  hydro(1H)azonine-                                                              thionocarboxylate                                                   137  0.07  Methyl-N-  4.48  Sorghum                                                                             40   10                                                  methyldithio-                                                                  carbanilate                                                              0.28  Methyl-N-  4.48  Sorghum                                                                             45   45                                                  methyldithio-                                                                  carbanilate                                                              1.12  Methyl-N-  4.48  Sorghum                                                                             65   35                                                  methyldithio-                                                                  carbanilate                                                         138  0.28  3-chloro-  4.48  Wheat                                                                                0   25                                                  2-butenyl-                                                                     carbanilate                                                              1.12  3-chloro-  4.48  Wheat                                                                               50   20                                                  2-butenyl-                                                                     carbanilate                                                              0.07  3-chloro-  4.48  Sorghum                                                                             30   20                                                  2-butenyl-                                                                     carbanilate                                                              0.28  3-chloro-  4.48  Sorghum                                                                             65   25                                                  2-butenyl-                                                                     carbanilate                                                              1.12  3-chloro-  4.48  Sorghum                                                                             70   30                                                  2-butenyl-                                                                     carbanilate                                                         139  0.14  Allylthiol-                                                                               4.48  Wheat                                                                               30   18                                                  carbamate                                                                0.14  Allylthiol-                                                                               4.48  Sorghum                                                                             65   32                                                  carbamate                                                           140  0.14  2-nitro-4- 4.48  Sorghum                                                                             50   47                                                  trifluoromethyl-                                                               phenyl-N,N-di-                                                                 methyldithiocar-                                                               bamate                                                              141  0.14  Allyl-N-   4.48  Wheat                                                                               15   33                                                  cyclohexyl-                                                                    thionocar-                                                                     banilate                                                                 0.84  Allyl-N-   4.48  Wheat                                                                               55   20                                                  cyclohexyl-                                                                    thionocar-                                                                     banilate                                                                 0.14  Allyl-N-   4.48  Sorghum                                                                             35   62                                                  cyclohexyl-                                                                    thionocar-                                                                     banilate                                                                 0.84  Allyl-N-   4.48  Sorghum                                                                             65   33                                                  cyclohexyl-                                                                    thionocar-                                                                     banilate                                                            142  0.14  Methyl-4-  4.48  Wheat                                                                               20   28                                                  morpholino-                                                                    carbodithioate                                                      143  0.14  Methyl-N-  4.48  Wheat                                                                               15   33                                                  butylcar-                                                                      banilate                                                                 0.84  Methyl-N-  4.48  Wheat                                                                               50   25                                                  butylcar-                                                                      banilate                                                            144  0.14  Allyl-N-   4.48  Wheat                                                                               15   33                                                  methylthiol-                                                                   carbamate                                                                0.14  Allyl-N-   4.48  Sorghum                                                                             50   47                                                  methylthiol-                                                                   carbamate                                                                0.84  Allyl-N-   4.48  Sorghum                                                                             75   23                                                  methylthiol-                                                                   carbamate                                                           145  0.28  2-chloro-  4.48  Sorghum                                                                             10    5                                                  allyl-N-iso-                                                                   butyldithio-                                                                   carbanilate                                                              0.56  2-chloro-  4.48  Sorghum                                                                             15   20                                                  allyl-N-iso-                                                                   butyldithio-                                                                   carbanilate                                                              1.12  2-chloro-  4.48  Sorghum                                                                             25   20                                                  allyl-N-iso-                                                                   butyldithio-                                                                   carbanilate                                                              2.24  2-chloro-  4.48  Sorghum                                                                             30   60                                                  allyl-N-iso-                                                                   butyldithio-                                                                   carbanilate                                                         146  0.28  2-chloro-  4.48  Sorghum                                                                             10    5                                                  allyl-p-chloro-                                                                dithiocarbanilate                                                        0.56  2-chloro-  4.48  Sorghum                                                                             15   20                                                  allyl-p-chloro-                                                                dithiocarbanilate                                                        2.24  2-chloro-  4.48  Sorghum                                                                             55   35                                                  allyl-p-chloro-                                                                dithiocarbanilate                                                   147  0.56  Methyl-p-  4.48  Sorghum                                                                             45   43                                                  methyl-N-methyl-                                                               dithiocarbanilate                                                        1.12  Methyl-p-  4.48  Sorghum                                                                             45   45                                                  methyl-N-methyl-                                                               dithiocarbanilate                                                        2.24  Methyl-p-  4.48  Sorghum                                                                             50   47                                                  methyl-N-methyl-                                                               dithiocarbanilate                                                        4.48  Methyl-p-  4.48  Sorghum                                                                             55   42                                                  methyl-N-methyl-                                                               dithiocarbanilate                                                   __________________________________________________________________________

                                      TABLE I (B)                                  __________________________________________________________________________                                         Per- Safen-                                   Acetan-      Antag-              cent ing                                   Ex.                                                                               ilide  Amount                                                                               onistic  Amount     Inhibi-                                                                             Effect                                No.                                                                               Herbicide                                                                             (kg./ha.)                                                                            Agent    (kg./ha.)                                                                            Crop tion (%)                                   __________________________________________________________________________     148                                                                               alachlor                                                                              4.48  Methyl-N-                                                                               4.48  Wheat                                                                               35   43                                                    methyl-O-                                                                      methyldithio- -     carbanilate                                   alachlor                                                                              4.48  Methyl-N-                                                                               4.48  Sorghum                                                                             75   20                                                    methyl-O-                                                                      methyldithio-                                                                  carbanilate                                                       butachlor                                                                             4.48  Methyl-N-                                                                               4.48  Wheat                                                                               10   33                                                    methyl-O-                                                                      methyldithio-                                                                  carbanilate                                                       butachlor                                                                             4.48  Methyl-N-                                                                               4.48  Sorghum                                                                             40   35                                                    methyl-O-                                                                      methyldithio-                                                                  carbanilate                                                    149                                                                               butachlor                                                                             4.48  Methyl-N-                                                                               4.48  Wheat                                                                               20   23                                                    ethyl-p-chloro-                                                                dithiocar-                                                                     banilate                                                          butachlor                                                                             4.48  Methyl-N-                                                                               4.48  Sorghum                                                                             45   30                                                    ethyl-p-chloro-                                                                dithiocar-                                                                     banilate                                                       150                                                                               alachlor                                                                              0.56  2-cyclo- 4.48  Sorghum                                                                             50   33                                                    hexen-1-yl-N-                                                                  methyldithio-                                                                  carbanilate                                                       alachlor                                                                              4.48  2-cyclo- 4.48  Sorghum                                                                             70   25                                                    hexen-1-yl-N-                                                                  methyldithio-                                                                  carbanilate                                                       butachlor                                                                             4.48  2-cyclo- 4.48  Sorghum                                                                             50   25                                                    hexen-1-yl-N-                                                                  methyldithio-                                                                  carbanilate                                                    151                                                                               butachlor                                                                             4.48  Ethyl-N- 4.48  Sorghum                                                                             65   20                                                    isopropyl-                                                                     carbanilate                                                    152                                                                               butachlor                                                                             0.56  Isopropyl-N-                                                                            4.48  Sorghum                                                                             15   25                                                    isopropylcar-                                                                  banilate                                                          butachlor                                                                             4.48  Isopropyl-                                                                              4.48  Sorghum                                                                             55   30                                                    N-isopropyl-                                                                   carbanilate                                                    153                                                                               butachlor                                                                             4.48  Methyl-N-                                                                               4.48  Sorghum                                                                             60   25                                                    isopropyl-                                                                     carbanilate                                                    154                                                                               butachlor                                                                             4.48  Butyl-N-iso-                                                                            4.48  Sorghum                                                                             70   15                                                    propylthiol-                                                                   carbanilate                                                    155                                                                               butachlor                                                                             4.48  o-fluoro-                                                                               4.48  Sorghum                                                                             60   25                                                    benzyl-N-                                                                      methyldithio-                                                                  carbanilate                                                    156                                                                               butachlor                                                                             4.48  m-fluoro-                                                                               4.48  Sorghum                                                                             70   15                                                    benzyl-N-                                                                      methyldithio-                                                                  carbanilate                                                    157                                                                               butachlor                                                                             4.48  m-trifluoro-                                                                            4.48  Wheat                                                                               10   35                                                    methylbenzyl-                                                                  N-methyldithio-                                                                carbanilate                                                       butachlor                                                                             0.56  m-trifluoro-                                                                            4.48  Sorghum                                                                             20   20                                                    methylbenzyl-                                                                  N-methyldithio-                                                                carbanilate                                                       butachlor                                                                             4.48  m-trifluoro-                                                                            4.48  Sorghum                                                                             60   25                                                    methylbenzyl-                                                                  N-methyldithio-                                                                carbanilate                                                    158                                                                               butachlor                                                                             0.56  Benzyl-N-                                                                               4.48  Wheat                                                                                0   15                                                    butyldithio-                                                                   carbanilate                                                       butachlor                                                                             0.56  Benzyl-N-                                                                               4.48  Sorghum                                                                             20   20                                                    butyldithio-                                                                   carbanilate                                                    159                                                                               butachlor                                                                             4.48  Methyl-N-                                                                               4.48  Wheat                                                                               20   25                                                    propyldithio-                                                                  carbanilate                                                       butachlor                                                                             4.48  Methyl-N-                                                                               4.48  Sorghum                                                                             45   40                                                    propyldithio-                                                                  carbanilate                                                    160                                                                               alachlor                                                                              0.28  Allyl-N- 4.48  Sorghum                                                                             35   20                                                    propyldithio-                                                                  carbanilate                                                       butachlor                                                                             0.56  Allyl-N- 4.48  Sorghum                                                                             30   10                                                    propyldithio-                                                                  carbanilate                                                       butachlor                                                                             4.48  Allyl-N- 4.48  Sorghum                                                                             45   40                                                    propyldithio-                                                                  carbanilate                                                    161                                                                               alachlor                                                                              0.28  Methyl-N-                                                                               4.48  Sorghum                                                                             45   10                                                    propylthiol-                                                                   carbanilate                                                       alachlor                                                                              2.24  Methyl-N-                                                                               4.48  Sorghum                                                                             75   10                                                    propylthiol-                                                                   carbanilate                                                       butachlor                                                                             0.56  Methyl-N-                                                                               4.48  Sorghum                                                                             25   15                                                    propylthiol-                                                                   carbanilate                                                    162                                                                               butachlor                                                                             4.48  Ethyl-N- 4.48  Sorghum                                                                             70   15                                                    propylthiol-                                                                   carbanilate                                                    163                                                                               butachlor                                                                             4.48  Propyl-N-                                                                               4.48  Sorghum                                                                             70   15                                                    propylthiol-                                                                   carbanilate                                                    164                                                                               butachlor                                                                             4.48  Propyl-N-                                                                               4.48  Wheat                                                                               25   20                                                    propyldithio-                                                                  carbanilate                                                    165                                                                               butachlor                                                                             4.48  Allylthiono-                                                                            4.48  Sorghum                                                                             55   40                                                    carbanilate                                                    166                                                                               alachlor                                                                              2.24  Cyanoethyl-                                                                             4.48  Sorghum                                                                             45   25                                                    N-methyl-                                                                      dithio-                                                                        carbanilate                                                       butachlor                                                                             4.48  Cyanoethyl-                                                                             4.48  Sorghum                                                                             60   35                                                    N-methyl-                                                                      dithio-                                                                        carbanilate                                                    167                                                                               butachlor                                                                             4.48  Butyl-N- 4.48  Sorghum                                                                             50   45                                                    isopropyl-                                                                     dithio-                                                                        carbanilate                                                    168                                                                               butachlor                                                                             0.56  Methyl-N-                                                                               4.48  Wheat                                                                                0   10                                                    isopropyl-                                                                     dithio-                                                                        carbanilate                                                       butachlor                                                                             4.48  Methyl-N-                                                                               4.48  Wheat                                                                               20   25                                                    isopropyl-                                                                     dithio-                                                                        carbanilate                                                    169                                                                               butachlor                                                                             4.48  Butyl-N- 4.48  Sorghum                                                                             70   25                                                    isopropyl-                                                                     carbanilate                                                    170                                                                               butachlor                                                                             4.48  Propyl-N-                                                                               4.48  Sorghum                                                                             70   25                                                    isopropyl-                                                                     carbanilate                                                    171                                                                               butachlor                                                                             4.48  Allyl-m- 4.48  Sorghum                                                                             65   23                                                    chlorodithio-                                                                  carbanilate                                                    172                                                                               butachlor                                                                             0.56  2-chloro-                                                                               4.48  Sorghum                                                                             20   20                                                    allyldithio-                                                                   carbanilate                                                    173                                                                               alachlor                                                                              0.28  Allylthiono-                                                                            4.48  Wheat                                                                               20   35                                                    carbanilate                                                       butachlor                                                                             0.56  Allylthiono-                                                                            4.48  Sorghum                                                                             45   38                                                    carbanilate                                                       butachlor                                                                             2.24  Allylthiono-                                                                            4.48  Sorghum                                                                             60   33                                                    carbanilate                                                       butachlor                                                                             8.96  Allylthiono-                                                                            4.48  Sorghum                                                                             70   28                                                    carbanilate                                                    174                                                                               butachlor                                                                             0.56  Isopropyl-                                                                              4.48  Sorghum                                                                             50   33                                                    N-butyl-                                                                       carbanilate                                                       butachlor                                                                             2.24  Isopropyl-                                                                              4.48  Sorghum                                                                             70   23                                                    N-butyl-                                                                       carbanilate                                                    175                                                                               alachlor                                                                              0.56  Allyl-N- 4.48  Sorghum                                                                             60   25                                                    methyldithio-                                                                  carbanilate                                                       alachlor                                                                              1.12  Allyl-N- 4.48  Sorghum                                                                             75   20                                                    methyldithio-                                                                  carbanilate                                                       butachlor                                                                             0.56  Allyl-N- 4.48  Sorghum                                                                             20   63                                                    methyldithio-                                                                  carbanilate                                                       butachlor                                                                             2.24  Allyl-N- 4.48  Sorghum                                                                             50   43                                                    methyldithio-                                                                  carbanilate                                                       butachlor                                                                             8.96  Allyl-N- 4.48  Sorghum                                                                             60   38                                                    methyldithio-                                                                  carbanilate                                                    176                                                                               alachlor                                                                              0.28  Methyl-N-                                                                               4.48  Wheat                                                                                0   55                                                    ethyldithio-                                                                   carbanilate                                                       alachlor                                                                              1.12  Methyl-N-                                                                               4.48  Wheat                                                                               45   48                                                    ethyldithio-                                                                   carbanilate                                                       alachlor                                                                              4.48  Methyl-N-                                                                               4.48  Wheat                                                                               70   30                                                    ethyldithio-                                                                   carbanilate                                                       alachlor                                                                              0.28  Methyl-N-                                                                               4.48  Sorghum                                                                             60   33                                                    ethyldithio-                                                                   carbanilate                                                       butachlor                                                                             0.56  Methyl-N-                                                                               4.48  Sorghum                                                                             50   33                                                    ethyldithio-                                                                   carbanilate                                                       butachlor                                                                             2.24  Methyl-N-                                                                               4.48  Sorghum                                                                             70   23                                                    ethyldithio-                                                                   carbanilate                                                    177                                                                               2'-t-butyl                                                                            4.48  Allylthiono-                                                                            4.48  Wheat                                                                               40   40                                    6'-methyl-                                                                               carbanilate                                                             2-bromo-                                                                       acetanilide                                                                    N-butoxy-                                                                             0.28  Allylthiono-                                                                            4.48  Wheat                                                                               40   33                                       methyl-2'    carbanilate                                                    t-butyl-                                                                          6'-methyl-                                                                     acetanilide                                                                 178                                                                               2'-t-butyl                                                                            1.12  Isopropyl-                                                                              4.48  Wheat                                                                               35   25                                    6'-methyl-                                                                               N-butyl-                                                                2-bromo-     carbanilate                                                       acetanilide                                                                    2'-t-butyl                                                                            0.28  Isopropyl-                                                                              4.48  Sorghum                                                                             30   67                                    6'-methyl-                                                                               N-butyl                                                                 2-bromo-     carbanilate                                                       acetanilide                                                                 179                                                                               2'-t-butyl                                                                            0.28  Allyl-N- 4.48  Wheat                                                                               70   27                                    6'-methyl-                                                                               methyldithio-                                                           2-bromo-     carbanilate                                                       acetanilide                                                                    N-butoxy-                                                                             0.28  Allyl-N- 4.48  Wheat                                                                               40   33                                       methyl-2'    methyldithio-                                                  t-butyl-  carbanilate                                                             6'-methyl-                                                                     acetanilide                                                                    N-butoxy-                                                                             0.28  Allyl-N- 4.48  Sorghum                                                                             35   63                                       methyl-2'    methyldithio-                                                  t-butyl-  carbanilate                                                             6'-methyl-                                                                     acetanilide                                                                 180                                                                               2'-t-butyl                                                                            0.28  Methyl-N-                                                                               4.48  Wheat                                                                                0   10                                    6'-methyl-                                                                               ethyldithio-                                                            2-bromo-     carbanilate                                                       acetanilide                                                                    2'-t-butyl                                                                            1.12  Methyl-N-                                                                               4.48  Wheat                                                                               30   30                                    6'-methyl-                                                                               ethyldithio-                                                            2-bromo-     carbanilate                                                       acetanilide                                                                    N-butoxy-                                                                             0.28  Methyl-N-                                                                               4.48  Wheat                                                                               40   33                                       methyl-2'    ethyldithio-                                                   t-butyl-  carbanilate                                                             6'-methyl-                                                                     acetanilide                                                                    N-butoxy-                                                                             1.12  Methyl-N-                                                                               4.48  Wheat                                                                               65   28                                       methyl-2'    ethyldithio-                                                   t-butyl-  carbanilate                                                             6'-methyl-                                                                     acetanilide                                                                    N-butoxy-                                                                             0.28  Methyl-N-                                                                               4.48  Sorghum                                                                             70   28                                       methyl-2'    ethyldithio-                                                   t-butyl-  carbanilate                                                             6'-methyl-                                                                     acetanilide                                                                 __________________________________________________________________________

In the tables herein, the columns headed Percent Inhibition contain the observations of test pans of plants which quantify the response of plants to a combination treatment of acentanilide herbicide and safening agent. Likewise, the columns headed Safening Effect (%) contain the difference between the response of plants to treatment with acetanilide herbicide and the response of plants to a combination treatment of the same acetanilide herbicide and safening agent. Although in the foregoing examples the safening agent is applied to the soil before the acetanilide herbicide, equivalent results are obtainable when the safening agent is applied in mixture with the acetanilide herbicide or in sequence after the acetanilide herbicide is applied. This also is observed in post-emergent applications. The ability to be applied as mixtures and obtain safening of acetanilide herbicide with wheat and sorghum is confirmed in tank mix tests.

A key contribution of the present invention is that the safening or antagonistic agents when applied to seed reduce crop injury without reducing effective weed control by the acetanilide herbicides.

EXAMPLE 181

The procedure employed in Examples 1 through 180 is repeated except that neither the herbicide nor the antagonistic agents are incorporated into the soil, but rather the soil is placed over sorghum and weed seeds, the herbicide is sprayed on the surface of the soil, the antagonistic agent is then sprayed on the surface of the soil and then water from overhead is added to a depth of 6.3 mm. across the surface of each pan. Thereafter, until observation of results, water is added from below by subirrigation. All weeds are substantially controlled. The safening effect on sorghum is shown in Table II.

                  TABLE II                                                         ______________________________________                                         Amount of                     Per-                                             alachlor                                                                               Antago-               cent                                             Herbicide                                                                              nistic      Amount    Inhibi-                                                                               Safening                                  (kg./ha.)                                                                              Agent       (kg./ha.) tion   Effect(%)                                 ______________________________________                                         0.28    Isopropyl-  4.48      30     60                                                N-butylcar-                                                                    banilate                                                               0.56    Isopropyl-  4.48      20     75                                                N-butylcar-                                                                    banilate                                                               1.12    Isopropyl   4.48      85     12                                                N-butylcar-                                                                    banilate                                                               2.24    Isopropyl   4.48      70     29                                                N-butylcar-                                                                    banilate                                                               0.28    Methyl-N-   4.48      30     60                                                ethyldithio-                                                                   carbanilate                                                            0.56    Methyl-N-   4.48      55     40                                                ethyldithio-                                                                   carbanilate                                                            1.12    Methyl-N-   4.48      80     17                                                ethyldithio-                                                                   carbanilate                                                            2.24    Methyl-N-   4.48      90      9                                                ethyldithio-                                                                   carbanilate                                                            ______________________________________                                    

EXAMPLE 182

The primary use of acetanilideherbicides is for preemergent control of weeds by application of the herbicide to the soil before the plants emerge. This example illustrates the safening effect on alachlor herbicide when applied as a postemergent treatment on weeds in a crop of sorghum. Excellent weed control is shown with a substantial reduction in crop injury by the herbicide. The herbicide and antagonistic agent to be tested are applied in spray form to plants of a given age of several grasses and broadleaf species. In this test, one week after the plants are planted, each aluminum pan of plants is sprayed with a given volume of a solution of the desired percent concentration of the herbicide and antagonistic agent in sequence. The solution of safening agent is prepared by weighing the appropriate amount of agent in a suitable container, dissolving the safening agent in acetone and mixing the acetone solution with an approximately equal volume of water. The mixture of water and acetone solution is sprayed on the plants. The acetanilide herbicide along with a suitable emulsifying agent is dispersed in a suitable amount of water. The resulting water emulsion is then sprayed on the plants. The injuries to the plants are then observed approximately 21 days later and the results are recorded as percent inhibition of the plant. The results observed with respect to sorghum injury are presented in Table III.

EXAMPLE 183

The procedure of Example 182 is repeated except that the antagonistic agent is applied as a seed treatment rather than as a sequential spray before application of the herbicide. For seed treatment, the antagonistic agent is mixed with an inert carrier comprising a finely-divided clay and a high surface area calcium silicate in a range of weight percentages of active antagonistic agent to inert carrier. An excess of the antagonistic agent/inert carrier mixture is thoroughly mixed with the crop seed to be protected. With respect to sorghum seed, the following correlation of the composition of the mixture to the quantity of active ingredient per unit weight of sorghum seed is observed.

    ______________________________________                                         Percent by weight Percent by weight                                            of active antago- of active antago-                                            nistic agent to   nistic agent to                                              inert carrier (%  sorghum seed after                                           composition)      treatment (% on seed)                                        ______________________________________                                          1.25                 0.125                                                     2.5                  0.25                                                      5                    0.5                                                      10                    1.0                                                      ______________________________________                                    

The results of applying antagonistic agents as a seed treatment of sorghum seed at various percentages and applying alachlor herbicide as a post-emergent herbicide at various application rates is shown in Table IV. Good control of weed species is observed.

                  TABLE III                                                        ______________________________________                                         Amount of                     Per-                                             alachlor  Antago-             cent                                             Herbicide nistic     Amount   Inhibi-                                                                               Safening                                  (kg./ha.) Agent      (kg./ha.)                                                                               tion   Effect (%)                                ______________________________________                                         2.24    Isopropyl-N- 0.28     15     30                                                butylcarbanilate                                                       2.24    Isopropyl-N- 1.12     25     20                                                butylcarbanilate                                                       2.24    Isopropyl-N- 4.48     20     25                                                butylcarbanilate                                                       2.24    Methyl-N-ethyl-                                                                             0.28     20     25                                                dithiocarbanilate                                                      ______________________________________                                    

                  TABLE IV                                                         ______________________________________                                         Amount of            % On Seed                                                 alachlor  Antago-    Of Antago-                                                                               Percent                                         Herbicide nistic     nistic    Inhibi-                                                                              Safening                                  (kg./ha.) Agent      Agent     tion  Effect (%)                                ______________________________________                                         1.12    Isopropyl-N-  0.25     28    45                                                butylcarbanilate                                                       2.24    Isopropyl-N-  0.25     43    37                                                butylcarbanilate                                                       4.48    Isopropyl-N-  0.25     50    20                                                butylcarbanilate                                                       1.12    Isopropyl-N-  1.00     58    15                                                butylcarbanilate                                                       2.24    Isopropyl-N-  1.00     58    22                                                butylcarbanilate                                                       4.48    Isopropyl-N-  1.00     60    10                                                butylcarbanilate                                                       1.12    Methyl-N-ethyl-                                                                              0.125    33    40                                                dithiocarbanilate                                                      2.24    Methyl-N-ethyl-                                                                              0.125    75     5                                                dithiocarbanilate                                                      1.12    Methyl-N-ethyl-                                                                              0.50     53    20                                                dithiocarbanilate                                                      2.24    Methyl-N-ethyl-                                                                              0.50     58    22                                                dithiocarbanilate                                                      0.56    Allyl-N-methyl-                                                                              0.25     15    38                                                dithiocarbanilate                                                      1.12    Allyl-N-methyl-                                                                              0.25     35    50                                                dithiocarbanilate                                                      2.24    Allyl-N-methyl-                                                                              0.25     63    30                                                dithiocarbanilate                                                      4.48    Allyl-N-methyl-                                                                              0.25     85    10                                                dithiocarbanilate                                                      0.56    Allyl-N-methyl-                                                                              1.00     10    43                                                dithiocarbanilate                                                      1.12    Allyl-N-methyl-                                                                              1.00     20    65                                                dithiocarbanilate                                                      2.24    Allyl-N-methyl-                                                                              1.00     40    53                                                dithiocarbanilate                                                      4.48    Allyl-N-methyl-                                                                              1.00     78    17                                                dithiocarbanilate                                                      ______________________________________                                    

EXAMPLES 184-202

These examples illustrate the application of the antagonistic agents of this invention as seed treatments to protect desired crops from herbicidal injury by acetanilide herbicides. In these examples the herbicide is applied to the soil as in Example 1-180. However, the antagonistic agent is applied to crop seed as in Example 183. The results are tabulated in Table V which show the safening effect of the antagonistic agents of this invention.

In order to counteract injury by the selective acetanilide herbicide, the crop seed need be treated with only a small amount of the antagonistic agent. For example, application rates of about 1100 g. to as low as about 1.5 g. of active agent per bushel of seed may be used. The presently preferred application rate is in the range of about 3 g. to 550 g. of agent per bushel. The seed is treated with an antagonistic agent by use of conventional seed treating apparatus well known to the art. The seed is thoroughly mixed with the antagonistic agent in the seed treating apparatus, thereby giving a seed which is coated with the agent.

Since only a very small amount of active antagonistic agent is required for the seed treatment, the compound preferably is formulated as a wettable powder or an emulsifiable concentrate which can be diluted with water by the seed treater for use in the seed treating apparatus. Of course, under certain conditions, it may be desirable to dissolve the antagonistic agent in an organic solvent for use as a seed treatment or the pure compound alone may be used under properly controlled conditions.

There are thus also provided by this invention novel seed treating compositions containing one or more of the described active antagonistic agents intimately dispersed in an inert carrier or diluent for the intended use. Such carriers may be either solids, such as talc, clay, diatomaceous earth, sawdust, calcium carbonate, and the like or liquids such as water, kerosene, acetone, benzene, toluene, xylene, and the like in which the active agent may be either dissolved or dispersed. Emulsifying agents are advisably used to achieve a suitable emulsion if two immiscible liquids are used as a carrier. Wetting agents may also be used to aid in dispersing the active antagonistic agent in liquids used as a carrier in which the agent is not completely soluble. Emulsifying agents and wetting agents, also known as "surface active agents," are sold under numerous tradenames and may be either pure compounds, mixtures of compounds of the same general groups, or they may be mixtures of compounds of different classes. Typical satisfactory surface active agents which may be used are alkali metal higher alkylarylsulfonates such as sodium dodecylbenzenesulfonate and the soldium salts of alkylnaphthalenesulfonic acids, fatty alcohol sulfates such as the sodium salts of monoesters of sulfuric acid with n-aliphatic alcohols containing 8-18 carbon atoms, long chain quaternary ammonium compounds, sodium salts of petroleum-derived alkylsulfonic acids, polyethylene sorbitan monooleate, alkylaryl polyether alcohols, water-soluble lignin sulfonate salts, alkali-casein compositions, long chain alcohols usually containing 10 to 18 carbon atoms, and condensation products of ethylene oxide with fatty acids, alkylphenols and mercaptans.

                                      TABLE V                                      __________________________________________________________________________          Amount of                Per-                                                  alachlor                                                                               Antago- Weight   cent Safening                                    Example                                                                             Herbicide                                                                              nistic  % on     Inhibi-                                                                             Effect                                      Number                                                                              (kg./ha.)                                                                              Agent   Seed Crop                                                                               tion (%)                                         __________________________________________________________________________     184  0.28  Isopropyl-N-                                                                             0.25                                                                               Sorghum                                                                              0   78                                                     butylcarbani-                                                                  late                                                                     0.28  Isopropyl-N-                                                                             0.50                                                                               Sorghum                                                                              0   78                                                     butylcarbani-                                                                  late                                                                     0.28  Isopropyl-N-                                                                             1.00                                                                               Sorghum                                                                              5   73                                                     butylcarbani-                                                                  late                                                                     0.56  Isopropyl-N-                                                                             0.25                                                                               Sorghum                                                                              0   75                                                     butylcarbani-                                                                  late                                                                     0.56  Isopropyl-N-                                                                             0.50                                                                               Sorghum                                                                              5   70                                                     butylcarbani-                                                                  late                                                                     0.56  Isopropyl-N-                                                                             1.00                                                                               Sorghum                                                                             10   65                                                     butylcarbani-                                                                  late                                                                     1.12  Isopropyl-N-                                                                             0.25                                                                               Sorghum                                                                              0   93                                                     butylcarbani-                                                                  late                                                                     1.12  Isopropyl-N-                                                                             0.50                                                                               Sorghum                                                                              0   93                                                     butylcarbani-                                                                  late                                                                     1.12  Isopropyl-N-                                                                             1.00                                                                               Sorghum                                                                             10   83                                                     butylcarbani-                                                                  late                                                                     2.24  Isopropyl-N-                                                                             0.25                                                                               Sorghum                                                                             25   75                                                     butylcarbani-                                                                  late                                                                     2.24  Isopropyl-N-                                                                             0.50                                                                               Sorghum                                                                              0   100                                                    butylcarbani-                                                                  late                                                                     2.24  Isopropyl-N-                                                                             1.00                                                                               Sorghum                                                                              0   100                                                    butylcarbani-                                                                  late                                                                185  0.28  Methyldiethyl-                                                                           0.25                                                                               Wheat                                                                                0   13                                                     thionocar-                                                                     bamate                                                                   0.28  Methyldiethyl-                                                                           0.50                                                                               Wheat                                                                                0   13                                                     thionocar-                                                                     bamate                                                                   0.28  Methyldiethyl-                                                                           0.25                                                                               Sorghum                                                                             55   23                                                     thionocar-                                                                     bamate                                                                   0.28  Methyldiethyl-                                                                           0.50                                                                               Sorghum                                                                             65   13                                                     thionocar-                                                                     bamate                                                              186  0.28  Methyl-N- 0.25                                                                               Wheat                                                                                0   13                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N- 0.25                                                                               Wheat                                                                                5   10                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N- 0.25                                                                               Wheat                                                                                0   15                                                     ethyldithio-                                                                   carbanilate                                                              0.28  Methyl-N- 0.25                                                                               Sorghum                                                                             25   53                                                     ethyldithio-                                                                   carbanilate                                                              0.28  Methyl-N- 0.50                                                                               Sorghum                                                                             30   48                                                     ethyldithio-                                                                   carbanilate                                                              0.28  Methyl-N- 1.00                                                                               Sorghum                                                                             35   43                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N- 0.25                                                                               Sorghum                                                                             25   50                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N- 0.50                                                                               Sorghum                                                                             40   35                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N- 1.00                                                                               Sorghum                                                                             40   35                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N- 0.25                                                                               Sorghum                                                                             25   68                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N- 0.50                                                                               Sorghum                                                                             25   68                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N- 1.00                                                                               Sorghum                                                                             30   63                                                     ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N- 0.25                                                                               Sorghum                                                                             40   60                                                     ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N- 0.50                                                                               Sorghum                                                                             25   75                                                     ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N- 1.00                                                                               Sorghum                                                                             50   50                                                     ethyldithio-                                                                   carbanilate                                                         187  0.28  Isopropyl-N-                                                                             0.016                                                                              Sorghum                                                                             45   30                                                     butylcarbani-                                                                  late                                                                     0.28  Isopropyl-N-                                                                             0.031                                                                              Sorghum                                                                             35   40                                                     butylcarbani-                                                                  late                                                                     0.28  Isopropyl-N-                                                                             0.063                                                                              Sorghum                                                                             35   40                                                     butylcarbani-                                                                  late                                                                     0.28  Isopropyl-N-                                                                             0.125                                                                              Sorghum                                                                             10   65                                                     butylcarbani-                                                                  late                                                                     0.28  Isopropyl-N-                                                                             0.25                                                                               Sorghum                                                                             15   60                                                     butylcarbani-                                                                  late                                                                     0.56  Isopropyl-N-                                                                             0.016                                                                              Sorghum                                                                             45   40                                                     butylcarbani-                                                                  late                                                                     0.56  Isopropyl-N-                                                                             0.031                                                                              Sorghum                                                                             50   35                                                     butylcarbani-                                                                  late                                                                     0.56  Isopropyl-                                                                               0.063                                                                              Sorghum                                                                             40   45                                                     N-butylcar-                                                                    banilate                                                                 0.56  Isopropyl-                                                                               0.125                                                                              Sorghum                                                                             15   70                                                     N-butylcar-                                                                    banilate                                                                 0.56  Isopropyl-                                                                               0.250                                                                              Sorghum                                                                             18   67                                                     N-butylcar-                                                                    banilate                                                                 1.12  Isopropyl-                                                                               0.016                                                                              Sorghum                                                                             65   27                                                     N-butylcar-                                                                    banilate                                                                 1.12  Isopropyl-                                                                               0.031                                                                              Sorghum                                                                             55   37                                                     N-butylcar-                                                                    banilate                                                                 1.12  Isopropyl-                                                                               0.063                                                                              Sorghum                                                                             50   42                                                     N-butylcar-                                                                    banilate                                                                 1.12  Isopropyl-                                                                               0.125                                                                              Sorghum                                                                             25   67                                                     N-butylcar-                                                                    banilate                                                                 1.12  Isopropyl-                                                                               0.250                                                                              Sorghum                                                                             40   52                                                     N-butylcar-                                                                    banilate                                                                 2.24  Isopropyl-                                                                               0.016                                                                              Sorghum                                                                             85    8                                                     N-butylcar-                                                                    banilate                                                                 2.24  Isopropyl-                                                                               0.031                                                                              Sorghum                                                                             85    8                                                     N-butylcar-                                                                    banilate                                                                 2.24  Isopropyl-                                                                               0.063                                                                              Sorghum                                                                             50   43                                                     N-butylcar-                                                                    banilate                                                                 2.24  Isopropyl-                                                                               0.125                                                                              Sorghum                                                                             40   53                                                     N-butylcar-                                                                    banilate                                                                 2.24  Isopropyl-                                                                               0.250                                                                              Sorghum                                                                             35   58                                                     N-butylcar-                                                                    banilate                                                            188  0.28  Methyl-N- 0.016                                                                              Sorghum                                                                             65   10                                                     ethyldithio-                                                                   carbanilate                                                              0.28  Methyl-N- 0.031                                                                              Sorghum                                                                             50   25                                                     ethyldithio-                                                                   carbanilate                                                              0.28  Methyl-N- 0.063                                                                              Sorghum                                                                             20   55                                                     ethyldithio-                                                                   carbanilate                                                              0.28  Methyl-N- 0.125                                                                              Sorghum                                                                             15   60                                                     ethyldithio-                                                                   carbanilate                                                              0.28  Methyl-N- 0.250                                                                              Sorghum                                                                             30   45                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N- 0.016                                                                              Sorghum                                                                             65   20                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N- 0.031                                                                              Sorghum                                                                             50   35                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N- 0.063                                                                              Sorghum                                                                             25   60                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N- 0.125                                                                              Sorghum                                                                             20   65                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Methyl-N- 0.250                                                                              Sorghum                                                                             35   50                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N- 0.016                                                                              Sorghum                                                                             65   27                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N- 0.031                                                                              Sorghum                                                                             70   22                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N- 0.063                                                                              Sorghum                                                                             40   52                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N- 0.125                                                                              Sorghum                                                                             35   57                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Methyl-N- 0.250                                                                              Sorghum                                                                             35   57                                                     ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N- 0.016                                                                              Sorghum                                                                             80   13                                                     ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N- 0.031                                                                              Sorghum                                                                             75   18                                                     ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N- 0.063                                                                              Sorghum                                                                             60   33                                                     ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N- 0.125                                                                              Sorghum                                                                             40   53                                                     ethyldithio-                                                                   carbanilate                                                              2.24  Methyl-N- 0.250                                                                              Sorghum                                                                             35   58                                                     ethyldithio-                                                                   carbanilate                                                         189  0.14  Allylthio-                                                                               0.016                                                                              Sorghum                                                                             70   15                                                     nocarbani-                                                                     late                                                                     0.14  Allylthio-                                                                               0.063                                                                              Sorghum                                                                             45   40                                                     nocarbani-                                                                     late                                                                     0.28  Allylthio-                                                                               0.063                                                                              Sorghum                                                                             65   34                                                     nocarbani-                                                                     late                                                                190  0.14  Allyl-N-  0.016                                                                              Sorghum                                                                             75   20                                                     methyldithio-                                                                  carbanilate                                                              0.14  Allyl-N-  0.063                                                                              Sorghum                                                                             20   75                                                     methyldithio-                                                                  carbanilate                                                              0.14  Allyl-N-  0.250                                                                              Sorghum                                                                             25   70                                                     methyldithio-                                                                  carbanilate                                                              0.14  Allyl-N-  1.00                                                                               Sorghum                                                                             10   85                                                     methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-  0.063                                                                              Sorghum                                                                             40   45                                                     methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-  0.250                                                                              Sorghum                                                                             25   60                                                     methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-  1.00                                                                               Sorghum                                                                             25   60                                                     methyldithio-                                                                  carbanilate                                                              0.56  Allyl-N-  0.063                                                                              Sorghum                                                                             40   58                                                     methyldithio-                                                                  carbanilate                                                              0.56  Allyl-N-  0.250                                                                              Sorghum                                                                             25   73                                                     methyldithio-                                                                  carbanilate                                                              0.56  Allyl-N-  1.00                                                                               Sorghum                                                                             20   78                                                     methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-  0.063                                                                              Sorghum                                                                             50   50                                                     methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-  0.250                                                                              Sorghum                                                                             45   55                                                     methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-  1.00                                                                               Sorghum                                                                             45   55                                                     methyldithio-                                                                  carbanilate                                                              2.24  Allyl-N-  0.063                                                                              Sorghum                                                                             65   35                                                     methyldithio-                                                                  carbanilate                                                              2.24  Allyl-N-  0.250                                                                              Sorghum                                                                             60   40                                                     methyldithio-                                                                  carbanilate                                                              2.24  Allyl-N-  1.00                                                                               Sorghum                                                                             55   45                                                     methyldithio-                                                                  carbanilate                                                         191  0.28  Allyl-    0.25                                                                               Wheat                                                                               30   13                                                     thiono-                                                                        carbanilate                                                              0.56  Allyl-    0.25                                                                               Wheat                                                                               15   48                                                     thiono-                                                                        carbanilate                                                              1.12  Allyl-    0.25                                                                               Wheat                                                                               40   33                                                     thiono-                                                                        carbanilate                                                              2.24  Allyl-    0.25                                                                               Wheat                                                                               55   25                                                     thiono-                                                                        carbanilate                                                              4.48  Allyl-    0.25                                                                               Wheat                                                                               60   33                                                     thiono-                                                                        carbanilate                                                         192  0.28  Allyl-N-  1.00                                                                               Wheat                                                                               20   23                                                     methyldithio-                                                                  carbanilate                                                              0.56  Allyl-N-  1.00                                                                               Wheat                                                                               25   38                                                     methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-  1.00                                                                               Wheat                                                                               55   28                                                     methyldithio-                                                                  carbanilate                                                              2.24  Allyl-N-  1.00                                                                               Wheat                                                                               65   15                                                     methyldithio-                                                                  carbanilate                                                              4.48  Allyl-N-  1.00                                                                               Wheat                                                                               65   28                                                     methyldithio-                                                                  carbanilate                                                         193  0.28  2-Chloroallyl-                                                                           1.00                                                                               Wheat                                                                               10   33                                                     o-chloro-N-(2-                                                                 chloroallyl)di-                                                                thiocarbanilate                                                          0.56  2-Chloroallyl-                                                                           1.00                                                                               Wheat                                                                               15   48                                                     o-chloro-N-(2-                                                                 chloroallyl)di-                                                                thiocarbanilate                                                          1.12  2-Chloroallyl-                                                                           1.00                                                                               Wheat                                                                               25   48                                                     o-chloro-N-(2-                                                                 chloroallyl)di-                                                                thiocarbanilate                                                          2.24  2-Chloroallyl-                                                                           1.00                                                                               Wheat                                                                               45   35                                                     o-chloro-N-(2-                                                                 chloroallyl)di-                                                                thiocarbanilate                                                          4.48  2-Chloroallyl-                                                                           1.00                                                                               Wheat                                                                               60   33                                                     o-chloro-N-(2-                                                                 chloroallyl)di-                                                                thiocarbanilate                                                     194  0.28  Allyl-N-  0.063                                                                              Wheat                                                                               15   35                                                     methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-  0.25                                                                               Wheat                                                                               30   20                                                     methyldithio-                                                                  carbanilate                                                              0.56  Allyl-N-  0.25                                                                               Wheat                                                                               60   10                                                     methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-  0.25                                                                               Wheat                                                                               60   15                                                     methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-  1.00                                                                               Wheat                                                                               30   20                                                     methyldithio-                                                                  carbanilate                                                              0.56  Allyl-N-  1.00                                                                               Wheat                                                                               40   30                                                     methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-  1.00                                                                               Wheat                                                                               60   15                                                     methyldithio-                                                                  carbanilate                                                         195  0.14  2-chloroallyl-                                                                           0.016                                                                              Wheat                                                                                0   25                                                     o-chloro-N-                                                                    (2-chloroallyl)                                                                dithiocarbanilate                                                        0.56  2-chloroallyl-                                                                           0.016                                                                              Wheat                                                                               40   20                                                     o-chloro-N-                                                                    (2-chloroallyl)                                                                dithiocarbanilate                                                        0.14  2-chloroallyl-                                                                           0.063                                                                              Wheat                                                                                0   25                                                     o-chloro-N-                                                                    (2-chloroallyl)                                                                dithiocarbanilate                                                        0.14  2-chloroallyl-                                                                           0.25                                                                               Wheat                                                                                0   25                                                     o-chloro-N-                                                                    (2-chloroallyl)                                                                dithiocarbanilate                                                        0.28  2-chloroallyl-                                                                           0.25                                                                               Wheat                                                                               20   30                                                     o-chloro-N-                                                                    (2-chloroallyl)                                                                dithiocarbanilate                                                        1.12  2-chloroallyl-                                                                           0.25                                                                               Wheat                                                                               60   15                                                     o-chloro-N-                                                                    (2-chloroallyl)                                                                dithiocarbanilate                                                   196  0.07  Allyl-N-  1.0 Sorghum                                                                              5   75                                                     methyldithio-                                                                  carbanilate                                                              0.14  Allyl-N-  1.0 Sorghum                                                                              0   90                                                     methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-  1.0 Sorghum                                                                             10   85                                                     methyldithio-                                                                  carbanilate                                                              0.56  Allyl-N-  1.0 Sorghum                                                                             15   85                                                     methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-  1.0 Sorghum                                                                             25   75                                                     methyldithio-                                                                  carbanilate                                                              2.24  Allyl-N-  1.0 Sorghum                                                                             40   60                                                     methyldithio-                                                                  carbanilate                                                              0.07  Allyl-N-  2.0 Sorghum                                                                              0   80                                                     methyldithio-                                                                  carbanilate                                                              0.14  Allyl-N-  2.0 Sorghum                                                                              0   90                                                     methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-  2.0 Sorghum                                                                             10   85                                                     methyldithio-                                                                  carbanilate                                                              0.56  Allyl-N-  2.0 Sorghum                                                                             15   85                                                     methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-  2.0 Sorghum                                                                             15   85                                                     methyldithio-                                                                  carbanilate                                                              2.24  Allyl-N-  2.0 Sorghum                                                                             40   60                                                     methyldithio-                                                                  carbanilate                                                              0.07  Allyl-N-  4.0 Sorghum                                                                              5   75                                                     methyldithio-                                                                  carbanilate                                                              0.14  Allyl-N-  4.0 Sorghum                                                                              0   90                                                     methyldithio-                                                                  carbanilate                                                              0.28  Allyl-N-  4.0 Sorghum                                                                             10   85                                                     methyldithio-                                                                  carbanilate                                                              0.56  Allyl-N-  4.0 Sorghum                                                                             20   80                                                     methyldithio-                                                                  carbanilate                                                              1.12  Allyl-N-  4.0 Sorghum                                                                             20   80                                                     methyldithio-                                                                  carbanilate                                                              2.24  Allyl-N-  4.0 Sorghum                                                                             40   60                                                     methyldithio-                                                                  carbanilate                                                         197  0.28  2-Cyclohex-                                                                              0.25                                                                               Wheat                                                                               40   20                                                     en-1-yldiiso-                                                                  propylthiolcar-                                                                bamate                                                              198  0.14  Isopropylhex-                                                                            0.063                                                                              Wheat                                                                               15   15                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                       0.28  Isopropylhex-                                                                            0.063                                                                              Wheat                                                                               20   30                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                       0.56  Isopropylhex-                                                                            0.063                                                                              Wheat                                                                               30   50                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                       1.12  Isopropylhex-                                                                            0.063                                                                              Wheat                                                                               35   40                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                       2.24  Isopropylhex-                                                                            0.063                                                                              Wheat                                                                               65   20                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                       0.14  Isopropylhex-                                                                            0.25                                                                               Wheat                                                                               15   15                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                       0.28  Isopropylhex-                                                                            0.25                                                                               Wheat                                                                               20   30                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                       0.56  Isopropylhex-                                                                            0.25                                                                               Wheat                                                                               20   60                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                       1.12  Isopropylhex-                                                                            0.25                                                                               Wheat                                                                               30   45                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                       2.24  Isopropylhex-                                                                            0.25                                                                               Wheat                                                                               40   45                                                     ahydroazocine-1                                                                (2H)-carbothionate                                                  199  0.14  Ethyloctahydro-                                                                          0.063                                                                              Wheat                                                                                0   15                                                     (1H)azoninecar-                                                                bothionate                                                               0.28  Ethyloctahydro-                                                                          0.063                                                                              Wheat                                                                                5   60                                                     (1H)azoninecar-                                                                bothionate                                                               0.56  Ethylocta-                                                                               0.063                                                                              Wheat                                                                               20   45                                                     hydro(1H)azo-                                                                  ninecarbothionate                                                        1.12  Ethylocta-                                                                               0.063                                                                              Wheat                                                                               15   55                                                     hydro(1H)azo-                                                                  ninecarbothionate                                                        2.24  Ethylocta-                                                                               0.063                                                                              Wheat                                                                               60   20                                                     hydro(1H)azo-                                                                  ninecarbothionate                                                        0.14  Ethylocta-                                                                               0.25                                                                               Wheat                                                                                0   15                                                     hydro(1H)azo-                                                                  ninecarbothionate                                                        0.28  Ethylocta-                                                                               0.25                                                                               Wheat                                                                               25   40                                                     hydro(1H)azo-                                                                  ninecarbothionate                                                        0.56  Ethylocta-                                                                               0.25                                                                               Wheat                                                                               20   45                                                     hydro(1H)azo-                                                                  ninecarbothionate                                                        1.12  Ethylocta-                                                                               0.25                                                                               Wheat                                                                               25   45                                                     hydro(1H)azo-                                                                  ninecarbothionate                                                        2.24  Ethylocta-                                                                               0.25                                                                               Wheat                                                                               35   45                                                     hydro(1H)azo-                                                                  ninecarbothionate                                                   200  0.14  Benzyliso-                                                                               0.063                                                                              Wheat                                                                               10   15                                                     butyldithio-                                                                   carbamate                                                                0.28  Benzyliso-                                                                               0.063                                                                              Wheat                                                                               20   45                                                     butyldithio-                                                                   carbamate                                                                0.56  Benzyliso-                                                                               0.063                                                                              Wheat                                                                               30   45                                                     butyldithio-                                                                   carbamate                                                                0.28  Benzyliso-                                                                               0.25                                                                               Wheat                                                                               15   50                                                     butyldithio-                                                                   carbamate                                                                0.56  Benzyliso-                                                                               0.25                                                                               Wheat                                                                               15   60                                                     butyldithio-                                                                   carbamate                                                                1.12  Benzyliso-                                                                               0.25                                                                               Wheat                                                                               30   40                                                     butyldithio-                                                                   carbamate                                                                2.24  Benzyliso-                                                                               0.25                                                                               Wheat                                                                               50   30                                                     butyldithio-                                                                   carbamate                                                           201  0.14  Methyl-N- 0.063                                                                              Wheat                                                                                0   10                                                     methyldithio-                                                                  carbanilate                                                              0.28  Methyl-N- 0.063                                                                              Wheat                                                                                0   55                                                     methyldithio-                                                                  carbanilate                                                              0.56  Methyl-N- 0.063                                                                              Wheat                                                                               45   20                                                     methyldithio-                                                                  carbanilate                                                              1.12  Methyl-N- 0.063                                                                              Wheat                                                                               55   35                                                     methyldithio-                                                                  carbanilate                                                              2.24  Methyl-N- 0.063                                                                              Wheat                                                                               60   30                                                     methyldithio-                                                                  carbanilate                                                              0.14  Methyl-N- 0.25                                                                               Wheat                                                                                0   10                                                     methyldithio-                                                                  carbanilate                                                              0.28  Methyl-N- 0.25                                                                               Wheat                                                                                0   55                                                     methyldithio-                                                                  carbanilate                                                              0.56  Methyl-N- 0.25                                                                               Wheat                                                                                0   65                                                     methyldithio-                                                                  carbanilate                                                              1.12  Methyl-N- 0.25                                                                               Wheat                                                                               15   75                                                     methyldithio-                                                                  carbanilate                                                              2.24  Methyl-N- 0.25                                                                               Wheat                                                                               25   65                                                     methyldithio-                                                                  carbanilate                                                              0.28  Methyl-N- 1.0 Wheat                                                                               20   35                                                     methyldithio-                                                                  carbanilate                                                              0.56  Methyl-N- 1.0 Wheat                                                                               15   50                                                     methyldithio-                                                                  carbanilate                                                              1.12  Methyl-N- 1.0 Wheat                                                                               25   65                                                     methyldithio-                                                                  carbanilate                                                              2.24  Methyl-N- 1.0 Wheat                                                                               25   65                                                     methyldithio-                                                                  carbanilate                                                         202  0.14  Phenyldi- 0.25                                                                               Sorghum                                                                              0   15                                                     ethyldithio-                                                                   carbanilate                                                              0.28  Phenyldi- 0.25                                                                               Sorghum                                                                              0   35                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Phenyldi- 0.25                                                                               Sorghum                                                                             10   55                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Phenyldi- 0.25                                                                               Sorghum                                                                             15   75                                                     ethyldithio-                                                                   carbanilate                                                              0.56  Phenyldi- 1.0 Sorghum                                                                             40   25                                                     ethyldithio-                                                                   carbanilate                                                              1.12  Phenyldi- 1.0 Sorghum                                                                             50   40                                                     ethyldithio-                                                                   carbanilate                                                         __________________________________________________________________________

The safening results found in greenhouse tests are substantiated by field tests of a representative antagonistic agent, allyl-N-methyldithiocarbanilate. Good results are obtained when sorghum and wheat seed is treated with this antagonistic agent formulated with a variety of liquid carriers such as ketone solvents, for example acetone, chlorinated hydrocarbon solvents, for example dichloromethane, aromatic solvents, for example toluene and ester solvents, for example ethyl acetate, as well as a variety of solid diluents such as clays, silicates and combinations of clays and silicates. The preferred concentrations of solid formulations range from about 10 percent to about 50 percent by weight of active antagonistic agent to total formulation weight.

While this invention has been described with respect to certain embodiments, it is to be understood that it is not so limited and that variations and modifications thereof obvious to those skilled in the art to which this invention appertains can be made without departing from the spirit or scope thereof. 

What is claimed is:
 1. A method for reducing injury to crops by α-haloacetanilide herbicides which comprises applying to the soil, crop, or crop seed an effective safening amount of a compound of the formula ##STR10##wherein R is C₁₋₆ alkyl, C₂₋₈ alkenyl or haloalkenyl, phenyl, cyanomethyl, cyclohexyl, cyclohexenyl, benzyl or benzyl substituted with halo, nitro or trifluoromethyl groups; R¹ is C₁₋₈ alkyl, C₂₋₈ alkenyl, phenyl or phenyl substituted with halo, nitro or lower alkyl groups and R² is hydrogen, C₁₋₈ alkyl or C₂₋₈ alkenyl or haloalkenyl.
 2. A method of claim 1 wherein the crops are wheat and sorghum.
 3. A method of claim 1 wherein the acetanilide is α-chloroacetanilide.
 4. A method of claim 1 wherein the compound is applied to the soil.
 5. A method of claim 4 wherein the compound is applied to the soil and incorporated into the soil.
 6. A method of claim 4 wherein the compound is applied to the soil dispersed in a liquid carrier.
 7. A method of claim 4 wherein the compound is applied to the soil dispersed on a particulate solid carrier.
 8. A method of claim 1 wherein the compound is applied to the seed.
 9. A method of claim 8 wherein the compound is applied to the seed dispersed in a liquid carrier.
 10. A method of claim 8 wherein the compound is applied to the seed dispersed on a particulate solid carrier.
 11. A method of claim 1 wherein R¹ is phenyl or phenyl substituted with halo, nitro or lower alkyl groups.
 12. A method of claim 11 wherein R is C₁₋₆ alkyl.
 13. A method of claim 12 wherein R² is hydrogen.
 14. A method of claim 12 wherein R² is C₁₋₆ alkyl.
 15. A method of claim 12 wherein R² is C₂₋₈ alkenyl.
 16. A method of claim 12 wherein R² is C₂₋₈ haloalkenyl.
 17. A method of claim 11 wherein R is C₂₋₈ alkenyl.
 18. A method of claim 17 wherein R² is hydrogen.
 19. A method of claim 17 wherein R² is C₁₋₆ alkyl.
 20. A method of claim 17 wherein R² is C₂₋₈ alkenyl.
 21. A method of claim 17 wherein R² is C₂₋₈ haloalkenyl.
 22. A method of claim 11 wherein R is phenyl.
 23. A method of claim 1 wherein R is cyclohexyl or cyclohexenyl.
 24. A method of claim 11 wherein R is C₂₋₈ haloalkenyl.
 25. A method of claim 1 wherein R¹ is C₁₋₆ alkyl.
 26. A method of claim 25 wherein R is C₁₋₆ alkyl.
 27. A method of claim 26 wherein R² is C₁₋₆ alklyl.
 28. Method of claim 3 wherein said α-chloroacetanilide is alachlor.
 29. Method of claim 19 wherein said compound is allyl N-methyldithiocarbanilate.
 30. A method of claim 1 wherein R is benzyl or benzyl substituted with halogen or trifluoromethyl. 